DD254193A5 - Verfahren zur herstellung von carbonsaeurederivaten - Google Patents

Verfahren zur herstellung von carbonsaeurederivaten Download PDF

Info

Publication number: DD254193A5
Authority: DD; German Democratic Republic
Prior art keywords: chlorophenyl; acid; group; sulfonyl; methylphenyl
Prior art date: 1985-07-16

Application number

DD86292398A

Other languages

German (de)

English (en)

Inventor

Hans P Wolff

Ernst-Christian Witte

Hans-Frieder Kuehnle

Original Assignee

��@��@��k��

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.)

1985-07-16

Filing date

1986-07-11

Publication date

1988-02-17

1986-07-11 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1988-02-17 Publication of DD254193A5 publication Critical patent/DD254193A5/de

Links

238000000034 method Methods 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
239000001257 hydrogen Substances 0.000 claims abstract description 29
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
125000002947 alkylene group Chemical group 0.000 claims abstract description 12
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 11
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 10
229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
125000004442 acylamino group Chemical group 0.000 claims abstract description 3
-1 aryloxy radical Chemical class 0.000 claims description 120
150000001875 compounds Chemical class 0.000 claims description 52
239000000203 mixture Substances 0.000 claims description 43
238000006243 chemical reaction Methods 0.000 claims description 22
150000001735 carboxylic acids Chemical class 0.000 claims description 14
150000002148 esters Chemical class 0.000 claims description 14
150000003254 radicals Chemical group 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
150000001408 amides Chemical class 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
150000005840 aryl radicals Chemical class 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
238000009833 condensation Methods 0.000 claims description 7
230000005494 condensation Effects 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
238000006114 decarboxylation reaction Methods 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
150000002902 organometallic compounds Chemical class 0.000 claims description 3
150000003457 sulfones Chemical class 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 claims description 2
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
229920001577 copolymer Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
235000010265 sodium sulphite Nutrition 0.000 claims description 2
101000604097 Xenopus laevis Homeobox protein notochord Proteins 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 10
201000001320 Atherosclerosis Diseases 0.000 abstract description 5
208000008589 Obesity Diseases 0.000 abstract description 5
206010012601 diabetes mellitus Diseases 0.000 abstract description 5
235000020824 obesity Nutrition 0.000 abstract description 5
230000000144 pharmacologic effect Effects 0.000 abstract description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
239000012230 colorless oil Substances 0.000 description 55
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 50
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
239000000243 solution Substances 0.000 description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 17
239000002253 acid Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
SYFKSHQWENARTE-UHFFFAOYSA-N 1-(5-bromopentyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CCCCCBr)C=C1 SYFKSHQWENARTE-UHFFFAOYSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
125000000446 sulfanediyl group Chemical group *S* 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
VDXYJUBMHZEPOQ-UHFFFAOYSA-N ethyl 2-(4-methylphenyl)sulfonylacetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=C(C)C=C1 VDXYJUBMHZEPOQ-UHFFFAOYSA-N 0.000 description 12
150000002431 hydrogen Chemical class 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 11
239000000284 extract Substances 0.000 description 11
159000000000 sodium salts Chemical class 0.000 description 11
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 8
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000002585 base Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 5
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 5
150000001413 amino acids Chemical class 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000003814 drug Substances 0.000 description 5
TVQGDYNRXLTQAP-UHFFFAOYSA-N ethyl heptanoate Chemical compound CCCCCCC(=O)OCC TVQGDYNRXLTQAP-UHFFFAOYSA-N 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 5
238000007127 saponification reaction Methods 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
XQQDUAHAUITQJC-UHFFFAOYSA-N 2-bromo-7-(4-chlorophenyl)heptanoic acid Chemical compound OC(=O)C(Br)CCCCCC1=CC=C(Cl)C=C1 XQQDUAHAUITQJC-UHFFFAOYSA-N 0.000 description 4
PLFOOGQHKGHALM-UHFFFAOYSA-N 2-carbamoyl-7-(4-chlorophenyl)heptanoic acid Chemical compound NC(=O)C(C(O)=O)CCCCCC1=CC=C(Cl)C=C1 PLFOOGQHKGHALM-UHFFFAOYSA-N 0.000 description 4
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
NSELUZYKLBMGBD-UHFFFAOYSA-N ethyl 2-(4-methylphenyl)sulfonyloctanoate Chemical compound CCCCCCC(C(=O)OCC)S(=O)(=O)C1=CC=C(C)C=C1 NSELUZYKLBMGBD-UHFFFAOYSA-N 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000000126 substance Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
YONRPNKBFMFRLE-UHFFFAOYSA-N 7-(4-chlorophenyl)-2-(4-chlorophenyl)sulfonylheptanoic acid Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)C(C(=O)O)CCCCCC1=CC=C(Cl)C=C1 YONRPNKBFMFRLE-UHFFFAOYSA-N 0.000 description 3
DDDYMWYRGWBBNA-UHFFFAOYSA-N 7-(4-chlorophenyl)-2-(4-methylphenoxy)heptanoic acid Chemical compound C1=CC(C)=CC=C1OC(C(O)=O)CCCCCC1=CC=C(Cl)C=C1 DDDYMWYRGWBBNA-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
206010018429 Glucose tolerance impaired Diseases 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 3
208000001280 Prediabetic State Diseases 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000003513 alkali Substances 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
230000003178 anti-diabetic effect Effects 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
KGHGQPPADMKEKN-UHFFFAOYSA-N ethyl 2-(4-methylphenyl)sulfonylhexadecanoate Chemical compound CCCCCCCCCCCCCCC(C(=O)OCC)S(=O)(=O)C1=CC=C(C)C=C1 KGHGQPPADMKEKN-UHFFFAOYSA-N 0.000 description 3
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000004043 oxo group Chemical group O=* 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
201000009104 prediabetes syndrome Diseases 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000005809 transesterification reaction Methods 0.000 description 3
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 description 2
OVXYDNVSUOXGQG-UHFFFAOYSA-N 1-(3-bromopropyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CCCBr)C=C1 OVXYDNVSUOXGQG-UHFFFAOYSA-N 0.000 description 2
DPTVPYBSBNIACI-UHFFFAOYSA-N 1-(4-bromobutoxy)-4-chlorobenzene Chemical compound ClC1=CC=C(OCCCCBr)C=C1 DPTVPYBSBNIACI-UHFFFAOYSA-N 0.000 description 2
WVSYQCITZUEVAS-UHFFFAOYSA-N 1-(6-bromohexyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CCCCCCBr)C=C1 WVSYQCITZUEVAS-UHFFFAOYSA-N 0.000 description 2
MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
CLZRDHUBODXICN-UHFFFAOYSA-N 1-chloro-4-(3-chloroprop-1-enyl)benzene Chemical compound ClCC=CC1=CC=C(Cl)C=C1 CLZRDHUBODXICN-UHFFFAOYSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
WSIPJTYIMPZFAQ-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)S(=O)(=O)C1=CC=C(C)C=C1 WSIPJTYIMPZFAQ-UHFFFAOYSA-N 0.000 description 2
OXTQIQYVWBFDJP-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyloctanoic acid Chemical compound CCCCCCC(C(O)=O)S(=O)(=O)C1=CC=C(C)C=C1 OXTQIQYVWBFDJP-UHFFFAOYSA-N 0.000 description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 2
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AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 2
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AQZMHLUIPBFKEC-UHFFFAOYSA-N diethyl 2-[5-(4-chlorophenyl)pentyl]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)CCCCCC1=CC=C(Cl)C=C1 AQZMHLUIPBFKEC-UHFFFAOYSA-N 0.000 description 1
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239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
150000002084 enol ethers Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
YWISQMULUMKADV-UHFFFAOYSA-N ethyl 2-(3-chlorophenyl)sulfonylacetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=CC(Cl)=C1 YWISQMULUMKADV-UHFFFAOYSA-N 0.000 description 1
DYFAHQJFMQNAKC-UHFFFAOYSA-N ethyl 2-(4-cyanophenyl)sulfonylacetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=C(C#N)C=C1 DYFAHQJFMQNAKC-UHFFFAOYSA-N 0.000 description 1
HJUXYQLTIVYHIN-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonylacetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=C(OC)C=C1 HJUXYQLTIVYHIN-UHFFFAOYSA-N 0.000 description 1
HMJPGZAQKXEQCN-UHFFFAOYSA-N ethyl 2-(4-methylphenyl)sulfinylacetate Chemical compound CCOC(=O)CS(=O)C1=CC=C(C)C=C1 HMJPGZAQKXEQCN-UHFFFAOYSA-N 0.000 description 1
CLDKRUPMTQXUOZ-UHFFFAOYSA-N ethyl 2-(benzenesulfonyl)-5-(4-chlorophenyl)heptanoate Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C(=O)OCC)CCC(CC)C1=CC=C(Cl)C=C1 CLDKRUPMTQXUOZ-UHFFFAOYSA-N 0.000 description 1
NJBWORPRIRNTLH-UHFFFAOYSA-N ethyl 2-(benzenesulfonyl)acetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=CC=C1 NJBWORPRIRNTLH-UHFFFAOYSA-N 0.000 description 1
NPWXSAOSIKSMBQ-UHFFFAOYSA-N ethyl 2-(trifluoromethylsulfonyl)acetate Chemical compound CCOC(=O)CS(=O)(=O)C(F)(F)F NPWXSAOSIKSMBQ-UHFFFAOYSA-N 0.000 description 1
QVWPRJSMOVLNDQ-UHFFFAOYSA-N ethyl 2-[3-(trifluoromethyl)phenyl]sulfonylacetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 QVWPRJSMOVLNDQ-UHFFFAOYSA-N 0.000 description 1
SLIRLABNGAZSHX-UHFFFAOYSA-N ethyl 2-acetamido-2-cyanoacetate Chemical compound CCOC(=O)C(C#N)NC(C)=O SLIRLABNGAZSHX-UHFFFAOYSA-N 0.000 description 1
DGGKEEKFURNFHU-UHFFFAOYSA-N ethyl 2-acetamido-7-(4-chlorophenyl)-2-cyanoheptanoate Chemical compound CCOC(=O)C(C#N)(NC(C)=O)CCCCCC1=CC=C(Cl)C=C1 DGGKEEKFURNFHU-UHFFFAOYSA-N 0.000 description 1
BEAZAEKCFJBIGY-UHFFFAOYSA-N ethyl 2-acetyloxy-5-phenylpentanoate Chemical compound CCOC(=O)C(OC(C)=O)CCCC1=CC=CC=C1 BEAZAEKCFJBIGY-UHFFFAOYSA-N 0.000 description 1
ROXNCXUNLVAYJM-UHFFFAOYSA-N ethyl 2-amino-7-(4-chlorophenyl)heptanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(N)CCCCCC1=CC=C(Cl)C=C1 ROXNCXUNLVAYJM-UHFFFAOYSA-N 0.000 description 1
VZNCDMOOFRESPT-UHFFFAOYSA-N ethyl 2-carbonochloridoyl-7-(4-chlorophenyl)heptanoate Chemical compound CCOC(=O)C(C(Cl)=O)CCCCCC1=CC=C(Cl)C=C1 VZNCDMOOFRESPT-UHFFFAOYSA-N 0.000 description 1
OCCWQCYBCZADCE-UHFFFAOYSA-N ethyl 2-methylsulfonylacetate Chemical compound CCOC(=O)CS(C)(=O)=O OCCWQCYBCZADCE-UHFFFAOYSA-N 0.000 description 1
LUSDAPILDWACOV-UHFFFAOYSA-N ethyl 2-naphthalen-1-ylsulfonylacetate Chemical compound C1=CC=C2C(S(=O)(=O)CC(=O)OCC)=CC=CC2=C1 LUSDAPILDWACOV-UHFFFAOYSA-N 0.000 description 1
MIENQULAFJVGDO-UHFFFAOYSA-N ethyl 4-methyl-2-(4-methylphenyl)sulfonyl-5-phenylpent-4-enoate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)C(C(=O)OCC)CC(C)=CC1=CC=CC=C1 MIENQULAFJVGDO-UHFFFAOYSA-N 0.000 description 1
LWSBXZTUYKJSHZ-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-2-(4-methylphenyl)sulfonylpent-4-enoate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)C(C(=O)OCC)CC=CC1=CC=C(Cl)C=C1 LWSBXZTUYKJSHZ-UHFFFAOYSA-N 0.000 description 1
LGKNGZKHVGBJIC-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-2-(4-methylphenyl)sulfonylpent-4-ynoate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)C(C(=O)OCC)CC#CC1=CC=C(Cl)C=C1 LGKNGZKHVGBJIC-UHFFFAOYSA-N 0.000 description 1
NRTZRNNRJCSUQR-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-2-(trifluoromethylsulfonyl)heptanoate Chemical compound CCOC(=O)C(S(=O)(=O)C(F)(F)F)CCC(CC)C1=CC=C(Cl)C=C1 NRTZRNNRJCSUQR-UHFFFAOYSA-N 0.000 description 1
VXIJRHRQUNDUJC-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-2-cyanopentanoate Chemical compound CCOC(=O)C(C#N)CCCC1=CC=C(Cl)C=C1 VXIJRHRQUNDUJC-UHFFFAOYSA-N 0.000 description 1
TXAJOMZOGUICBU-UHFFFAOYSA-N ethyl 6-(4-chlorophenoxy)-2-(4-methylphenyl)sulfonylhexanoate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)C(C(=O)OCC)CCCCOC1=CC=C(Cl)C=C1 TXAJOMZOGUICBU-UHFFFAOYSA-N 0.000 description 1
LZJAZAGWANAPMA-UHFFFAOYSA-N ethyl 7-(4-chlorophenyl)-2-(3-chlorophenyl)sulfonylheptanoate Chemical compound C=1C=CC(Cl)=CC=1S(=O)(=O)C(C(=O)OCC)CCCCCC1=CC=C(Cl)C=C1 LZJAZAGWANAPMA-UHFFFAOYSA-N 0.000 description 1
QGKMMJQPVULXPS-UHFFFAOYSA-N ethyl 7-(4-chlorophenyl)-2-(4-chlorophenyl)sulfonylheptanoate Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)C(C(=O)OCC)CCCCCC1=CC=C(Cl)C=C1 QGKMMJQPVULXPS-UHFFFAOYSA-N 0.000 description 1
FRKZXVIQBKGXSC-UHFFFAOYSA-N ethyl 7-(4-chlorophenyl)-2-(4-methylphenyl)sulfonylheptanoate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)C(C(=O)OCC)CCCCCC1=CC=C(Cl)C=C1 FRKZXVIQBKGXSC-UHFFFAOYSA-N 0.000 description 1
CLKIIKDYPZBDHC-UHFFFAOYSA-N ethyl 7-(4-chlorophenyl)-2-(4-methylphenyl)sulfonyloxyheptanoate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)OC(C(=O)OCC)CCCCCC1=CC=C(Cl)C=C1 CLKIIKDYPZBDHC-UHFFFAOYSA-N 0.000 description 1
LSLVXBTUYANZNT-UHFFFAOYSA-N ethyl 7-(4-chlorophenyl)-2-[(4-methylphenyl)sulfonylamino]heptanoate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)NC(C(=O)OCC)CCCCCC1=CC=C(Cl)C=C1 LSLVXBTUYANZNT-UHFFFAOYSA-N 0.000 description 1
AYBLCJYOWAOUMV-UHFFFAOYSA-N ethyl 7-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenyl]sulfonylheptanoate Chemical compound C=1C=CC(C(F)(F)F)=CC=1S(=O)(=O)C(C(=O)OCC)CCCCCC1=CC=C(Cl)C=C1 AYBLCJYOWAOUMV-UHFFFAOYSA-N 0.000 description 1
SJSGOEZQNSVSLU-UHFFFAOYSA-N ethyl 7-(4-chlorophenyl)-2-cyanoheptanoate Chemical compound CCOC(=O)C(C#N)CCCCCC1=CC=C(Cl)C=C1 SJSGOEZQNSVSLU-UHFFFAOYSA-N 0.000 description 1
KAFBSXORAPQZEB-UHFFFAOYSA-N ethyl 7-(4-chlorophenyl)-2-hydroxy-2-methylheptanoate Chemical compound CCOC(=O)C(C)(O)CCCCCC1=CC=C(Cl)C=C1 KAFBSXORAPQZEB-UHFFFAOYSA-N 0.000 description 1
BTJMPNSFOLLHKB-UHFFFAOYSA-N ethyl 7-(4-chlorophenyl)-2-hydroxyheptanoate Chemical compound CCOC(=O)C(O)CCCCCC1=CC=C(Cl)C=C1 BTJMPNSFOLLHKB-UHFFFAOYSA-N 0.000 description 1
MFRXJQHEWMSSAD-UHFFFAOYSA-N ethyl 7-(4-methylphenyl)-2-(4-methylphenyl)sulfonylheptanoate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)C(C(=O)OCC)CCCCCC1=CC=C(C)C=C1 MFRXJQHEWMSSAD-UHFFFAOYSA-N 0.000 description 1
NDILGUFIXZGYMV-UHFFFAOYSA-N ethyl 8-(4-chlorophenyl)-2-cyanooctanoate Chemical compound CCOC(=O)C(C#N)CCCCCCC1=CC=C(Cl)C=C1 NDILGUFIXZGYMV-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000003977 halocarboxylic acids Chemical class 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229940125396 insulin Drugs 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
WWDXAVNLFSVTDJ-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-5-phenylpent-4-enoate Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C(=O)OC)CC=CC1=CC=CC=C1 WWDXAVNLFSVTDJ-UHFFFAOYSA-N 0.000 description 1
JAPQSNKQUZZUKQ-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-2-(4-methylphenyl)sulfanylheptanoate Chemical compound C=1C=C(C)C=CC=1SC(C(=O)OC)CCCCCC1=CC=C(Cl)C=C1 JAPQSNKQUZZUKQ-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
BOZILQFLQYBIIY-INTXDZFKSA-N mevinic acid Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)CCC=C21 BOZILQFLQYBIIY-INTXDZFKSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000003001 serine protease inhibitor Substances 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 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
DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical class OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000001549 tubercolostatic effect Effects 0.000 description 1
239000000814 tuberculostatic agent Substances 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Emergency Medicine (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)
Pyrane Compounds (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD86292398A 1985-07-16 1986-07-11 Verfahren zur herstellung von carbonsaeurederivaten DD254193A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853525284 DE3525284A1 (de)	1985-07-16	1985-07-16	Neue carbonsaeurederivate, verfahren zu ihrer herstellung, ihre verwendung sowie arzneimittel, die diese verbindungen enthalten

Publications (1)

Publication Number	Publication Date
DD254193A5 true DD254193A5 (de)	1988-02-17

Family

ID=6275845

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86292398A DD254193A5 (de)	1985-07-16	1986-07-11	Verfahren zur herstellung von carbonsaeurederivaten

Country Status (21)

Country	Link
US (1)	US4933367A (fr)
EP (1)	EP0226636B1 (fr)
JP (1)	JPS63500310A (fr)
KR (1)	KR870700599A (fr)
AT (1)	ATE40681T1 (fr)
AU (2)	AU595814B2 (fr)
CA (1)	CA1316922C (fr)
DD (1)	DD254193A5 (fr)
DE (2)	DE3525284A1 (fr)
DK (1)	DK100487A (fr)
ES (1)	ES2001163A6 (fr)
FI (1)	FI871143A0 (fr)
GR (1)	GR861803B (fr)
IL (1)	IL79379A0 (fr)
NO (1)	NO166939C (fr)
NZ (1)	NZ216830A (fr)
PH (1)	PH25313A (fr)
PT (1)	PT82987B (fr)
SU (1)	SU1708156A3 (fr)
WO (1)	WO1987000521A2 (fr)
ZA (1)	ZA865192B (fr)

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DE4112103C2 (de) *	1991-02-18	1994-07-14	Matthias Mueller	Verwendung von Essigsäure zur Regulierung der Blutzuckerwerte
JP2785162B2 (ja) *	1991-04-05	1998-08-13	富士写真フイルム株式会社	写真用ポリエステル支持体およびハロゲン化銀写真感光材料
IL115995A0 (en) *	1994-11-15	1996-01-31	Bayer Ag	Substituted 4-biarylbutyric or 5-biarylpentanoic acids and derivatives as matrix metalloprotease inhibitors
US5789434A (en) *	1994-11-15	1998-08-04	Bayer Corporation	Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors
US6197791B1 (en)	1997-02-27	2001-03-06	American Cyanamid Company	N-hdroxy-2-(alkyl, aryl, or heteroaryl, sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors
US6172057B1 (en)	1997-02-27	2001-01-09	American Cyanamid Company	N-Hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors
US6262118B1 (en) *	1999-06-04	2001-07-17	Metabolex, Inc.	Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes and hyperlipidemia
US7576131B2 (en) *	1999-06-04	2009-08-18	Metabolex, Inc.	Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidemia and hyperuricemia
US6685951B2 (en)	2001-07-05	2004-02-03	R. T. Alamo Ventures I, Inc.	Administration of dihydroergotamine as a sublingual spray or aerosol for the treatment of migraine
US20030017175A1 (en) *	2001-07-05	2003-01-23	R.T. Alamo Ventures I, Inc.	Sublingual administration of dihydroergotamine for the treatment of migraine
US20030198669A1 (en) *	2001-07-05	2003-10-23	R.T. Alamo Ventures I, Llc	Compositions and methods for rapid dissolving formulations of dihydroergotamine and caffeine for the treatment of migraine
US6720450B2 (en)	2001-12-13	2004-04-13	North Carolina State University	Pesticidal activity of functionalized cyclopropanes
US7199259B2 (en) *	2003-06-20	2007-04-03	Metabolex, Inc.	Resolution of α-(phenoxy)phenylacetic acid derivatives
WO2005115384A2 (fr) *	2004-05-25	2005-12-08	Metabolex, Inc.	Triazoles substitués bicyliques comme modulateurs de ppar et méthodes de préparation
CN1997633A (zh) *	2004-05-25	2007-07-11	麦它波莱克斯股份有限公司	作为ppar调节剂的取代的三唑及其制备方法
US7714131B2 (en) *	2005-09-23	2010-05-11	Metabolex, Inc.	Process for the stereoselective preparation of (−)-halofenate and derivatives thereof
CA2702468A1 (fr) *	2007-10-12	2009-04-23	University Of Connecticut	Applications therapeutiques d'inhibiteurs d'hydrolase d'amide d'acide gras
CN114075106B (zh) *	2020-08-12	2023-09-12	广东省稀有金属研究所	一种脂肪醇醚羧酸的制备方法

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US3562330A (en)	1968-07-18	1971-02-09	Parke Davis & Co	2-phenoxy-4- and 5-phenyl-butyl and -pentyl-amines and salts
BE760034A (fr) *	1969-12-08	1971-06-08	Ici Ltd	Production d'esters
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1985
- 1985-07-16 DE DE19853525284 patent/DE3525284A1/de not_active Withdrawn
1986
- 1986-07-09 AU AU59880/86A patent/AU595814B2/en not_active Ceased
- 1986-07-10 AU AU61942/86A patent/AU6194286A/en not_active Abandoned
- 1986-07-10 US US07/027,229 patent/US4933367A/en not_active Expired - Fee Related
- 1986-07-10 JP JP61504316A patent/JPS63500310A/ja active Pending
- 1986-07-10 DE DE8686904797T patent/DE3662041D1/de not_active Expired
- 1986-07-10 AT AT86904797T patent/ATE40681T1/de active
- 1986-07-10 IL IL79379A patent/IL79379A0/xx not_active IP Right Cessation
- 1986-07-10 EP EP86904797A patent/EP0226636B1/fr not_active Expired
- 1986-07-10 GR GR861803A patent/GR861803B/el unknown
- 1986-07-10 WO PCT/EP1986/000406 patent/WO1987000521A2/fr not_active Ceased
- 1986-07-11 DD DD86292398A patent/DD254193A5/de not_active IP Right Cessation
- 1986-07-11 ZA ZA865192A patent/ZA865192B/xx unknown
- 1986-07-14 PH PH34010A patent/PH25313A/en unknown
- 1986-07-14 NZ NZ216830A patent/NZ216830A/en unknown
- 1986-07-15 CA CA000513766A patent/CA1316922C/fr not_active Expired - Fee Related
- 1986-07-15 PT PT82987A patent/PT82987B/pt not_active IP Right Cessation
- 1986-07-16 ES ES8600324A patent/ES2001163A6/es not_active Expired
1987
- 1987-02-26 DK DK100487A patent/DK100487A/da not_active Application Discontinuation
- 1987-03-13 NO NO871059A patent/NO166939C/no unknown
- 1987-03-13 SU SU874202278A patent/SU1708156A3/ru active
- 1987-03-16 FI FI871143A patent/FI871143A0/fi not_active Application Discontinuation
- 1987-03-16 KR KR870700223A patent/KR870700599A/ko not_active Ceased

Also Published As

Publication number	Publication date
DE3662041D1 (en)	1989-03-16
NO871059L (no)	1987-03-13
EP0226636A1 (fr)	1987-07-01
EP0226636B1 (fr)	1989-02-08
GR861803B (en)	1986-11-10
NO871059D0 (no)	1987-03-13
JPS63500310A (ja)	1988-02-04
DK100487D0 (da)	1987-02-26
PT82987A (de)	1986-08-01
SU1708156A3 (ru)	1992-01-23
ATE40681T1 (de)	1989-02-15
KR870700599A (ko)	1987-12-30
AU6194286A (en)	1987-02-10
FI871143A7 (fi)	1987-03-16
PH25313A (en)	1991-04-30
FI871143A0 (fi)	1987-03-16
AU5988086A (en)	1987-01-22
NO166939B (no)	1991-06-10
DE3525284A1 (de)	1987-01-29
CA1316922C (fr)	1993-04-27
NZ216830A (en)	1990-11-27
PT82987B (pt)	1988-07-01
ZA865192B (en)	1987-03-25
DK100487A (da)	1987-02-26
WO1987000521A3 (fr)	1987-03-12
ES2001163A6 (es)	1988-05-01
AU595814B2 (en)	1990-04-12
NO166939C (no)	1991-09-18
WO1987000521A2 (fr)	1987-01-29
IL79379A0 (en)	1986-10-31
US4933367A (en)	1990-06-12

Legal Events

Date	Code	Title	Description
2001-02-01	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD254193A5 (de)	1988-02-17	Verfahren zur herstellung von carbonsaeurederivaten
EP0612724B1 (fr)	1996-12-27	Benzène sulfonylurées et -thiourées substituées, procédé pour leur préparation et leur utilisation comme produits pharmaceutiques
DE19830430A1 (de)	2000-01-13	Schwefelsubstituierte Sulfonylamino-carbonsäure-N-arylamide, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
DE69105856T2 (de)	1995-05-11	Acetamidderivate.
EP0031954A2 (fr)	1981-07-15	Sulfonamides, procédé pour leur préparation et médicaments les contenant
DE2951135A1 (de)	1981-06-25	Sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung
DE10024319A1 (de)	2001-11-22	Bisacylguanidine
EP0384279B1 (fr)	1994-04-13	Benzène sulfonamides et procédé pour leur préparation
DE3872620T2 (de)	1992-12-03	(arylsulphonyl)-nitromethane, verfahren zu deren herstellung und deren verwendung in pharmazeutischen zusammensetzungen.
CN1071743C (zh)	2001-09-26	磺酰基或亚磺酰基苯甲酰基胍衍生物
DE3243158A1 (de)	1984-05-24	Neue sulfonsaeureester von hydroxycumarinen, ihre herstellung und sie enthaltende arzneimittel
EP0699660B1 (fr)	1998-10-28	Arylbenzoylguanidines
EP0279162B1 (fr)	1991-06-19	Dérivés d'acides carboniques, leur procédé de préparation et médicaments les contenant
EP1224166B1 (fr)	2003-09-17	Procede de fabrication de chlorhydrate de n-(4,5-bismethanesulfonyl-2-methyl-benzoyl)-guanidine
EP0242767B1 (fr)	1991-09-11	N-dihydroindolyléthyl-sulfonamides
DE3210063A1 (de)	1983-09-22	Sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung
PT98530B (pt)	1999-01-29	Processo para a preparacao de derivados de anilina e de composicoes farmaceuti-cas que os contem
DE10129704A1 (de)	2003-01-02	Verwendung von Benzolsulfonyl(thio)harnstoffen in der Behandlung des septischen Schocks
EP1658266B1 (fr)	2010-08-11	Benzoylguanidines a substitution pentafluorosulfanylphenyle, leurs procedes de production, leur utilisation en tant que medicaments ou agents de diagnostic, ainsi que medicament les contenant
DE3134780A1 (de)	1983-03-10	"sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung"
DE3232959A1 (de)	1984-03-08	Substituierte benzolsulfonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
EP0729954B1 (fr)	2003-09-03	Thiophénylurées et -thiourées, procédé pour leur préparation et leur utilisation comme médicament
DE69104304T2 (de)	1995-02-23	Amidobenzole.
AT266814B (de)	1968-12-10	Verfahren zur Herstellung von neuen Organosulffinyl- bzw. -sulfonylacylphenoxyalkansäuren und ihren Salzen
DD275454A5 (de)	1990-01-24	Verfahren zur herstellung von nitromethan