CA2062329A1 - Process and intermediates to 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acids - Google Patents
Process and intermediates to 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acidsInfo
- Publication number
- CA2062329A1 CA2062329A1 CA002062329A CA2062329A CA2062329A1 CA 2062329 A1 CA2062329 A1 CA 2062329A1 CA 002062329 A CA002062329 A CA 002062329A CA 2062329 A CA2062329 A CA 2062329A CA 2062329 A1 CA2062329 A1 CA 2062329A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- methyl
- formula
- compound
- intermediates
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 239000000543 intermediate Substances 0.000 title abstract description 21
- AVVACPBRCFXZMR-UHFFFAOYSA-N 2,2-dimethyl-3h-1-benzofuran-7-carboxylic acid Chemical class C1=CC(C(O)=O)=C2OC(C)(C)CC2=C1 AVVACPBRCFXZMR-UHFFFAOYSA-N 0.000 title abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 11
- 235000019253 formic acid Nutrition 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- LGSCEKCQFNKJSK-UHFFFAOYSA-N 2-methylprop-2-enyl 5-chloro-2-hydroxy-3-(2-methylprop-2-enyl)benzoate Chemical compound CC(=C)COC(=O)C1=CC(Cl)=CC(CC(C)=C)=C1O LGSCEKCQFNKJSK-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- FXYLOFIKRCWGQO-UHFFFAOYSA-N 2-methylprop-2-enyl 5-chloro-2-(2-methylprop-2-enoxy)benzoate Chemical compound CC(=C)COC(=O)C1=CC(Cl)=CC=C1OCC(C)=C FXYLOFIKRCWGQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- -1 bicyclic carboxylic esters Chemical class 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000000203 mixture 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
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N 12-hydroxylauric acid Chemical compound OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- 229960003390 magnesium sulfate Drugs 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- NKBASRXWGAGQDP-UHFFFAOYSA-N 5-chlorosalicylic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1O NKBASRXWGAGQDP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000005821 Claisen rearrangement reaction Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 229940005605 valeric acid Drugs 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/666,279 | 1991-03-07 | ||
| US07/666,279 US5142069A (en) | 1991-03-07 | 1991-03-07 | Process of preparing 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2062329A1 true CA2062329A1 (en) | 1992-09-08 |
Family
ID=24673565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002062329A Abandoned CA2062329A1 (en) | 1991-03-07 | 1992-03-05 | Process and intermediates to 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acids |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5142069A (enExample) |
| EP (1) | EP0502735B1 (enExample) |
| JP (1) | JPH04338381A (enExample) |
| KR (1) | KR100193973B1 (enExample) |
| AT (1) | ATE127461T1 (enExample) |
| BR (1) | BR9200768A (enExample) |
| CA (1) | CA2062329A1 (enExample) |
| DE (1) | DE69204497T2 (enExample) |
| DK (1) | DK0502735T3 (enExample) |
| ES (1) | ES2078652T3 (enExample) |
| GR (1) | GR3017875T3 (enExample) |
| HU (1) | HU212786B (enExample) |
| IE (1) | IE67382B1 (enExample) |
| IL (1) | IL101149A (enExample) |
| MX (1) | MX9200962A (enExample) |
| TW (1) | TW198014B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5723103A (en) * | 1994-12-09 | 1998-03-03 | Vanderbilt University | Substituted benzamides and radioligand analogs and methods of use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3860619A (en) * | 1969-05-09 | 1975-01-14 | Novo Terapeutisk Labor As | Sulphonylurea derivatives |
| WO1984003281A1 (en) * | 1983-02-19 | 1984-08-30 | Beecham Group Plc | Azabicycloalkyl benzamide and anilide derivatives |
| CA1297877C (en) * | 1983-12-22 | 1992-03-24 | Daniel Lednicer | Benzofurancarboxamides useful as antiemetic or antipsychotic agents |
| US4888353A (en) * | 1986-02-28 | 1989-12-19 | Erbamont, Inc. | Carboxamides useful as antiemetic or antipsychotic agents |
| US4921982A (en) * | 1988-07-21 | 1990-05-01 | Eli Lilly And Company | 5-halo-2,3-dihydro-2,2-dimethylbenzofuran-7-carboxylic acids useful as intermediates for 5-HT3 antagonists |
-
1991
- 1991-03-07 US US07/666,279 patent/US5142069A/en not_active Expired - Fee Related
- 1991-09-27 TW TW080107670A patent/TW198014B/zh active
-
1992
- 1992-03-05 AT AT92301904T patent/ATE127461T1/de not_active IP Right Cessation
- 1992-03-05 DE DE69204497T patent/DE69204497T2/de not_active Expired - Fee Related
- 1992-03-05 ES ES92301904T patent/ES2078652T3/es not_active Expired - Lifetime
- 1992-03-05 IL IL10114992A patent/IL101149A/en not_active IP Right Cessation
- 1992-03-05 KR KR1019920003610A patent/KR100193973B1/ko not_active Expired - Fee Related
- 1992-03-05 DK DK92301904.6T patent/DK0502735T3/da active
- 1992-03-05 CA CA002062329A patent/CA2062329A1/en not_active Abandoned
- 1992-03-05 EP EP92301904A patent/EP0502735B1/en not_active Expired - Lifetime
- 1992-03-05 HU HU9200745A patent/HU212786B/hu not_active IP Right Cessation
- 1992-03-05 MX MX9200962A patent/MX9200962A/es not_active IP Right Cessation
- 1992-03-06 JP JP4049416A patent/JPH04338381A/ja active Pending
- 1992-03-06 BR BR929200768A patent/BR9200768A/pt not_active IP Right Cessation
- 1992-03-06 IE IE920737A patent/IE67382B1/en not_active IP Right Cessation
-
1995
- 1995-10-25 GR GR950402980T patent/GR3017875T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69204497T2 (de) | 1996-03-21 |
| HU9200745D0 (en) | 1992-05-28 |
| US5142069A (en) | 1992-08-25 |
| IE920737A1 (en) | 1992-09-09 |
| IE67382B1 (en) | 1996-03-20 |
| BR9200768A (pt) | 1992-11-17 |
| EP0502735A1 (en) | 1992-09-09 |
| ATE127461T1 (de) | 1995-09-15 |
| HU212786B (en) | 1996-11-28 |
| DE69204497D1 (de) | 1995-10-12 |
| TW198014B (enExample) | 1993-01-11 |
| IL101149A0 (en) | 1992-11-15 |
| IL101149A (en) | 1996-09-12 |
| KR920018038A (ko) | 1992-10-21 |
| HUT61008A (en) | 1992-11-30 |
| GR3017875T3 (en) | 1996-01-31 |
| JPH04338381A (ja) | 1992-11-25 |
| EP0502735B1 (en) | 1995-09-06 |
| ES2078652T3 (es) | 1995-12-16 |
| DK0502735T3 (da) | 1996-04-09 |
| MX9200962A (es) | 1992-09-01 |
| KR100193973B1 (ko) | 1999-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU490290A3 (ru) | Способ получени производных пиримидин-6- ил -ацетоксиаминовой кислоты | |
| CA1143733A (en) | Producing 7-alkoxycarbonyl-6,8-dimethyl-4- hydroxymethyl-1-phthalazone and intermediates | |
| CA2062329A1 (en) | Process and intermediates to 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acids | |
| US4414416A (en) | Certain diacetyl-amino-phenolic derivatives | |
| US5019655A (en) | Method of preparing 4-dichlorophenyl-1-tetralones | |
| EP0858993B1 (en) | Method of producing keto acids | |
| US5177244A (en) | Process and intermediates to 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acids | |
| Zambias et al. | The Synthesis of 5-Hydroxy-2, 3-dihydrobenzo (B) thiophene (1) via an Efficient One Step Preparation of 5-Nitro-Benzo (B) thiophene-2-carboxylate (3A) | |
| AU689476B2 (en) | Process for preparing 1,2-diacyl-2-t-alkyl hydrazides | |
| US20060217565A1 (en) | Process for producing chromone compound | |
| JPH05155881A (ja) | ２−置換ベンゾ［ｂチオフェンおよびその中間体の製造方法 | |
| US4701528A (en) | Intermediates useful in the preparation of 3,4-dihydro-4-oxothieno[2,3-d]pyrimidine-2-carboxylates and process for preparing same | |
| KR950003333B1 (ko) | α,β-불포화케톤 및 케토옥심유도체 | |
| JP3118596B2 (ja) | アリールジアルキルチオカルバマート、２−メルカプトベンズアルデヒドおよび２−置換ベンゾ［ｂ］チオフェンの製造方法 | |
| JPH07238061A (ja) | 芳香族メトキシカルボン酸メチルエステルの製造方法 | |
| EP3640235B1 (en) | Process for the preparation of cyclic peri-succinoylacenaphthene and related 1,4-diketo compounds | |
| JP3646223B2 (ja) | 求電子反応による芳香族化合物の製造方法及び芳香族化合物 | |
| JP3961049B2 (ja) | ３−アミノ−４−（１−ヒドロキシアルキル）ピラゾリン化合物、その製造方法およびそれを使用した製造方法 | |
| JP2574083B2 (ja) | ３−ヒドロキシ−２−チオフェンカルボン酸誘導体の製造方法 | |
| JPS6310706B2 (enExample) | ||
| CA1151659A (en) | Producing 7-alkoxycarbonyl-6,8-dimethyl-4- hydroxymethyl-1-phthalazone and intermediates | |
| JPH0688939B2 (ja) | トリフルオロメチル安息香酸の製造法 | |
| JPH0812658A (ja) | シドノン類の製造法 | |
| SE448875B (sv) | 2-aroyl-(formyl)-substituerade pyrrolderivat och forfarande for framstellning derav | |
| JPH01233261A (ja) | ５−ハロ−３−プロピオニルサリチル酸低級アルキルエステルの精製法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |