IL97583A - Process for the dehydration of thio (piperidic acid-3,5-dicarboxylic acid ester, a specific ester of the tetrahydro-pyridicarboxylic acid - Google Patents
Process for the dehydration of thio (piperidic acid-3,5-dicarboxylic acid ester, a specific ester of the tetrahydro-pyridicarboxylic acidInfo
- Publication number
- IL97583A IL97583A IL9758391A IL9758391A IL97583A IL 97583 A IL97583 A IL 97583A IL 9758391 A IL9758391 A IL 9758391A IL 9758391 A IL9758391 A IL 9758391A IL 97583 A IL97583 A IL 97583A
- Authority
- IL
- Israel
- Prior art keywords
- bis
- acid
- piperidine
- compound
- dehydration
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 61
- 238000006297 dehydration reaction Methods 0.000 title claims abstract description 25
- 230000018044 dehydration Effects 0.000 title claims abstract description 22
- -1 tetrahydro pyridinedicarbothioic acid ester Chemical class 0.000 title claims description 31
- MKTWBGGZHLXSHE-UHFFFAOYSA-N 3,5-dioxa-4-thia-9-azabicyclo[5.3.1]undecane-2,6-dione Chemical class S1OC(=O)C2CNCC(C2)C(=O)O1 MKTWBGGZHLXSHE-UHFFFAOYSA-N 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 16
- 239000012024 dehydrating agents Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000004925 dihydropyridyl group Chemical class N1(CC=CC=C1)* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- GVBSRTBYUFJDIW-UHFFFAOYSA-N pyridine-3,5-dicarbothioic s-acid Chemical compound OC(=S)C1=CN=CC(C(O)=S)=C1 GVBSRTBYUFJDIW-UHFFFAOYSA-N 0.000 claims description 4
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 150000007970 thio esters Chemical class 0.000 claims description 3
- DXMOJTOODNTTMR-UHFFFAOYSA-N 1-hydroxypiperidine-3,5-dicarboxylic acid Chemical class ON1CC(CC(C1)C(=O)O)C(=O)O DXMOJTOODNTTMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 229940125904 compound 1 Drugs 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- BJKSVERSNVRTMF-UHFFFAOYSA-N piperidine-3,5-dicarbothioic s-acid Chemical compound SC(=O)C1CNCC(C(S)=O)C1 BJKSVERSNVRTMF-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 63
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 61
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 239000012973 diazabicyclooctane Substances 0.000 description 24
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000005796 dehydrofluorination reaction Methods 0.000 description 12
- IQDUSUMPAWCGJY-UHFFFAOYSA-N pyridine-2,3-dicarbothioic s-acid Chemical class SC(=O)C1=CC=CN=C1C(S)=O IQDUSUMPAWCGJY-UHFFFAOYSA-N 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 230000003197 catalytic effect Effects 0.000 description 9
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- TUDHHJQPQZFEIH-UHFFFAOYSA-N piperidine-4,4-diol Chemical class OC1(O)CCNCC1 TUDHHJQPQZFEIH-UHFFFAOYSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000012035 limiting reagent Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- IPIHCIXFZHQHKX-UHFFFAOYSA-N 2,6-dihydroxy-4-(2-methylpropyl)-2,6-bis(trifluoromethyl)piperidine-3,5-dicarbothioic s-acid Chemical compound CC(C)CC1C(C(O)=S)C(O)(C(F)(F)F)NC(O)(C(F)(F)F)C1C(O)=S IPIHCIXFZHQHKX-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- MXWKCJYCAHVAHK-UHFFFAOYSA-N 2h-pyran-2,3-diol Chemical class OC1OC=CC=C1O MXWKCJYCAHVAHK-UHFFFAOYSA-N 0.000 description 1
- RDOAUPPSCNSYPM-UHFFFAOYSA-N 3,4-dihydropyridine Chemical class C1CC=NC=C1 RDOAUPPSCNSYPM-UHFFFAOYSA-N 0.000 description 1
- BKVFOAJKAAHXEZ-UHFFFAOYSA-N 3-o,5-o-dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)pyridine-3,5-dicarbothioate Chemical compound COC(=S)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=S)OC)=C1CC(C)C BKVFOAJKAAHXEZ-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- RDTHWWKRUNOJBW-UHFFFAOYSA-N pyridine-2-carbodithioic acid Chemical compound SC(=S)C1=CC=CC=N1 RDTHWWKRUNOJBW-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49518190A | 1990-03-19 | 1990-03-19 | |
| US07/495,074 US5116991A (en) | 1990-03-19 | 1990-03-19 | Process for preparation of fluoromethyl-substituted dihydropyridine carbodithioates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL97583A0 IL97583A0 (en) | 1992-06-21 |
| IL97583A true IL97583A (en) | 1996-06-18 |
Family
ID=27051636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9758391A IL97583A (en) | 1990-03-19 | 1991-03-18 | Process for the dehydration of thio (piperidic acid-3,5-dicarboxylic acid ester, a specific ester of the tetrahydro-pyridicarboxylic acid |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0448542B1 (fr) |
| JP (1) | JP2514285B2 (fr) |
| KR (1) | KR930008234B1 (fr) |
| AT (1) | ATE130606T1 (fr) |
| AU (1) | AU630547B2 (fr) |
| CA (1) | CA2038435C (fr) |
| DE (1) | DE69114743T2 (fr) |
| ES (1) | ES2080287T3 (fr) |
| HU (2) | HU209737B (fr) |
| IL (1) | IL97583A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105130230A (zh) * | 2015-10-14 | 2015-12-09 | 马鞍山实达建材科技有限公司 | 一种平移式钛石膏煅烧方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0448541B1 (fr) * | 1990-03-19 | 1995-11-22 | Rohm And Haas Company | Procédé pour la préparation de pyridine carbodithioates, fluorométhyl substitués |
| US5055583A (en) * | 1990-03-19 | 1991-10-08 | Monsanto Company | Process for preparation of fluoromethyl-substituted piperidine carbodithioates |
| US5051512A (en) * | 1990-03-19 | 1991-09-24 | Monsanto Company | Process for preparation of fluoromethyl-substituted piperidine carbodithioates |
| DE10014607A1 (de) * | 2000-03-24 | 2001-09-27 | Bayer Ag | Verfahren zur Herstellung von unsymmetrischen 4,6-Bis(aryloxy pyrimidin-Derivaten |
| US8919422B2 (en) | 2011-02-18 | 2014-12-30 | United Technologies Corporation | Die casting system and cell |
| EP2821398A1 (fr) | 2013-07-03 | 2015-01-07 | Lonza Ltd | Procédé de préparation de dérivés d'acide 6-trifluorométhylpyridine-3-carboxylique à partir de 4,4,4-trifluoro-3-aminobutanoates |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES535014A0 (es) * | 1983-08-11 | 1985-08-01 | Monsanto Co | Un procedimiento para preparar derivados de piridina sustituidos en las posiciones 2 y 6 |
| ES8506276A1 (es) * | 1983-08-11 | 1985-07-01 | Monsanto Co | Un procedimiento para preparar dihidropiridinas |
| US4785129A (en) * | 1988-02-16 | 1988-11-15 | Monsanto Company | Methyl 4,4,4-trifluoro-3-oxo-butanethioate |
| EP0448541B1 (fr) * | 1990-03-19 | 1995-11-22 | Rohm And Haas Company | Procédé pour la préparation de pyridine carbodithioates, fluorométhyl substitués |
| US5055583A (en) * | 1990-03-19 | 1991-10-08 | Monsanto Company | Process for preparation of fluoromethyl-substituted piperidine carbodithioates |
| US5051512A (en) * | 1990-03-19 | 1991-09-24 | Monsanto Company | Process for preparation of fluoromethyl-substituted piperidine carbodithioates |
-
1991
- 1991-03-18 AU AU73505/91A patent/AU630547B2/en not_active Ceased
- 1991-03-18 HU HU91880A patent/HU209737B/hu unknown
- 1991-03-18 DE DE69114743T patent/DE69114743T2/de not_active Expired - Fee Related
- 1991-03-18 ES ES91870045T patent/ES2080287T3/es not_active Expired - Lifetime
- 1991-03-18 IL IL9758391A patent/IL97583A/en not_active IP Right Cessation
- 1991-03-18 AT AT91870045T patent/ATE130606T1/de not_active IP Right Cessation
- 1991-03-18 CA CA002038435A patent/CA2038435C/fr not_active Expired - Fee Related
- 1991-03-18 EP EP91870045A patent/EP0448542B1/fr not_active Expired - Lifetime
- 1991-03-18 KR KR1019910004257A patent/KR930008234B1/ko not_active Expired - Fee Related
- 1991-03-18 HU HU9401263A patent/HU212237B/hu not_active IP Right Cessation
- 1991-03-19 JP JP3216727A patent/JP2514285B2/ja not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105130230A (zh) * | 2015-10-14 | 2015-12-09 | 马鞍山实达建材科技有限公司 | 一种平移式钛石膏煅烧方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE130606T1 (de) | 1995-12-15 |
| EP0448542A2 (fr) | 1991-09-25 |
| HU209737B (en) | 1994-10-28 |
| IL97583A0 (en) | 1992-06-21 |
| HU9401263D0 (en) | 1994-08-29 |
| JP2514285B2 (ja) | 1996-07-10 |
| KR930008234B1 (ko) | 1993-08-27 |
| AU7350591A (en) | 1991-09-19 |
| EP0448542B1 (fr) | 1995-11-22 |
| JPH069563A (ja) | 1994-01-18 |
| HUT56821A (en) | 1991-10-28 |
| AU630547B2 (en) | 1992-10-29 |
| CA2038435C (fr) | 1997-10-14 |
| DE69114743T2 (de) | 1996-05-30 |
| KR910016705A (ko) | 1991-11-05 |
| EP0448542A3 (en) | 1992-03-11 |
| ES2080287T3 (es) | 1996-02-01 |
| CA2038435A1 (fr) | 1991-09-20 |
| DE69114743D1 (de) | 1996-01-04 |
| HU212237B (en) | 1996-05-28 |
| HU910880D0 (en) | 1991-09-30 |
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| Date | Code | Title | Description |
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| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |