NO790083L - Fremgangsmaate ved fremstilling av substituerte 1,4-cyclohexadien-carboxylsyrederivater - Google Patents

Fremgangsmaate ved fremstilling av substituerte 1,4-cyclohexadien-carboxylsyrederivater

Info

Publication number: NO790083L
Authority: NO; Norway
Prior art keywords: acid; straight; carbon atoms; chain; branched
Prior art date: 1978-01-12

Application number

NO790083A

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 NO790083L publication Critical patent/NO790083L/no

Links

238000000034 method Methods 0.000 title claims description 7
XCSQXCKDEVRTHN-UHFFFAOYSA-N cyclohexa-1,4-diene-1-carboxylic acid Chemical class OC(=O)C1=CCC=CC1 XCSQXCKDEVRTHN-UHFFFAOYSA-N 0.000 title description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 90
-1 3-amino-1,4-cyclohexadiene-carboxylic acid-trifluoroacetate Chemical compound 0.000 claims description 76
150000001875 compounds Chemical class 0.000 claims description 64
125000004432 carbon atom Chemical group C* 0.000 claims description 45
125000000217 alkyl group Chemical group 0.000 claims description 30
239000002585 base Substances 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 28
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
239000002904 solvent Substances 0.000 claims description 24
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 9
230000007062 hydrolysis Effects 0.000 claims description 9
238000006460 hydrolysis reaction Methods 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
150000008065 acid anhydrides Chemical class 0.000 claims description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
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 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
150000004820 halides Chemical class 0.000 claims description 6
HQKRXDWKEIDRLS-UHFFFAOYSA-N 3-aminocyclohexa-1,4-diene-1-carboxylic acid Chemical compound NC1C=CCC(C(O)=O)=C1 HQKRXDWKEIDRLS-UHFFFAOYSA-N 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
150000008064 anhydrides Chemical class 0.000 claims description 5
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 5
ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-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
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
239000012024 dehydrating agents‎ Substances 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
239000011630 iodine 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
DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 claims description 3
239000007787 solid Substances 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
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
239000007789 gas Substances 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
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
238000010306 acid treatment Methods 0.000 claims 2
FXMNVYBROILAKU-UHFFFAOYSA-N tert-butyl n-[cyano(phenyl)methylidene]carbamate Chemical compound CC(C)(C)OC(=O)N=C(C#N)C1=CC=CC=C1 FXMNVYBROILAKU-UHFFFAOYSA-N 0.000 claims 2
230000002378 acidificating effect Effects 0.000 claims 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
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BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
229960003692 gamma aminobutyric acid Drugs 0.000 description 18
OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
102000003929 Transaminases Human genes 0.000 description 13
108090000340 Transaminases Proteins 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture 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
239000012074 organic phase Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
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
125000002496 methyl group Chemical group [H]C([H])([H])* 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
239000004480 active ingredient Substances 0.000 description 5
229910021538 borax Inorganic materials 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
235000010339 sodium tetraborate Nutrition 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
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241000699670 Mus sp. Species 0.000 description 4
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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
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 3
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 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
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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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 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO790083A 1978-01-12 1979-01-11 Fremgangsmaate ved fremstilling av substituerte 1,4-cyclohexadien-carboxylsyrederivater NO790083L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US86885978A	1978-01-12	1978-01-12

Publications (1)

Publication Number	Publication Date
NO790083L true NO790083L (no)	1979-07-13

Family

ID=25352454

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO790083A NO790083L (no)	1978-01-12	1979-01-11	Fremgangsmaate ved fremstilling av substituerte 1,4-cyclohexadien-carboxylsyrederivater

Country Status (17)

Country	Link
JP (1)	JPS54100351A (da)
AU (1)	AU4260578A (da)
BE (1)	BE873411A (da)
DE (1)	DE2855931A1 (da)
DK (1)	DK12279A (da)
ES (1)	ES476712A1 (da)
FR (1)	FR2414493A1 (da)
GB (1)	GB2012268B (da)
IL (1)	IL56255A0 (da)
IT (1)	IT1113739B (da)
NL (1)	NL7900079A (da)
NO (1)	NO790083L (da)
NZ (1)	NZ189211A (da)
PH (1)	PH14294A (da)
PT (1)	PT69044A (da)
SE (1)	SE7813350L (da)
ZA (1)	ZA786944B (da)

Families Citing this family (3)

* 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
US5117338A (en) *	1991-09-26	1992-05-26	Mccrary Charles F	Jewelry lighting device
CN112740965B (zh) *	2021-01-07	2021-11-23	南京农业大学	不结球白菜“黄玫瑰”的周年转色方法

1978
- 1978-12-12 ZA ZA00786944A patent/ZA786944B/xx unknown
- 1978-12-15 AU AU42605/78A patent/AU4260578A/en active Pending
- 1978-12-18 NZ NZ189211A patent/NZ189211A/xx unknown
- 1978-12-19 IL IL56255A patent/IL56255A0/xx unknown
- 1978-12-23 DE DE19782855931 patent/DE2855931A1/de not_active Withdrawn
- 1978-12-28 SE SE7813350A patent/SE7813350L/xx unknown
1979
- 1979-01-05 NL NL7900079A patent/NL7900079A/xx not_active Application Discontinuation
- 1979-01-05 PH PH22020A patent/PH14294A/en unknown
- 1979-01-08 PT PT69044A patent/PT69044A/pt unknown
- 1979-01-10 ES ES476712A patent/ES476712A1/es not_active Expired
- 1979-01-11 IT IT47593/79A patent/IT1113739B/it active
- 1979-01-11 DK DK12279A patent/DK12279A/da not_active Application Discontinuation
- 1979-01-11 NO NO790083A patent/NO790083L/no unknown
- 1979-01-11 GB GB791001A patent/GB2012268B/en not_active Expired
- 1979-01-11 FR FR7900646A patent/FR2414493A1/fr not_active Withdrawn
- 1979-01-11 BE BE192839A patent/BE873411A/xx unknown
- 1979-01-12 JP JP141179A patent/JPS54100351A/ja active Pending

Also Published As

Publication number	Publication date
DK12279A (da)	1979-07-13
JPS54100351A (en)	1979-08-08
GB2012268A (en)	1979-07-25
PH14294A (en)	1981-05-04
IL56255A0 (en)	1979-03-12
IT7947593A0 (it)	1979-01-11
BE873411A (fr)	1979-05-02
GB2012268B (en)	1982-05-06
AU4260578A (en)	1979-07-19
NZ189211A (en)	1980-11-14
SE7813350L (sv)	1979-07-13
IT1113739B (it)	1986-01-20
ES476712A1 (es)	1979-12-01
ZA786944B (en)	1979-12-27
FR2414493A1 (fr)	1979-08-10
NL7900079A (nl)	1979-07-16
DE2855931A1 (de)	1979-07-19
PT69044A (en)	1979-02-01

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