NO823659L - Fremgangsmaate for fremstilling av antraniloyl-oksyalkanoater - Google Patents
Fremgangsmaate for fremstilling av antraniloyl-oksyalkanoaterInfo
- Publication number
- NO823659L NO823659L NO823659A NO823659A NO823659L NO 823659 L NO823659 L NO 823659L NO 823659 A NO823659 A NO 823659A NO 823659 A NO823659 A NO 823659A NO 823659 L NO823659 L NO 823659L
- Authority
- NO
- Norway
- Prior art keywords
- piperidyl
- carbon atoms
- substituted
- atom
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 42
- -1 4-piperidyl Chemical group 0.000 claims description 31
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 4
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 150000003053 piperidines Chemical class 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004436 sodium atom Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 239000000203 mixture Substances 0.000 description 11
- 159000000000 sodium salts Chemical class 0.000 description 10
- HTKGKUISLUERQX-UHFFFAOYSA-N 2-[(7-chloroquinolin-4-yl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 HTKGKUISLUERQX-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- JAYCBXVZZVTRDH-UHFFFAOYSA-N (1-methylpiperidin-3-yl) 2-chloroacetate;hydrochloride Chemical compound Cl.CN1CCCC(OC(=O)CCl)C1 JAYCBXVZZVTRDH-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- KPWYHWHRSMWDAK-UHFFFAOYSA-N (1-methyl-4-phenylpiperidin-4-yl) 2-chloroacetate;hydrochloride Chemical compound Cl.C1CN(C)CCC1(OC(=O)CCl)C1=CC=CC=C1 KPWYHWHRSMWDAK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- SPBVBDIOQVXDNI-UHFFFAOYSA-N (1-benzylpiperidin-4-yl) 2-chloroacetate;hydrochloride Chemical compound Cl.C1CC(OC(=O)CCl)CCN1CC1=CC=CC=C1 SPBVBDIOQVXDNI-UHFFFAOYSA-N 0.000 description 2
- UKANCZCEGQDKGF-UHFFFAOYSA-N 1-methylpiperidin-3-ol Chemical compound CN1CCCC(O)C1 UKANCZCEGQDKGF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- ABRFWVVJJXBTOA-UHFFFAOYSA-N [1-(2-phenylethyl)piperidin-4-yl] 2-chloroacetate;hydrochloride Chemical compound Cl.C1CC(OC(=O)CCl)CCN1CCC1=CC=CC=C1 ABRFWVVJJXBTOA-UHFFFAOYSA-N 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ORJQHLZQXNJZQL-UHFFFAOYSA-N (1-ethylpiperidin-4-yl) 2-chloroacetate;hydrochloride Chemical compound Cl.CCN1CCC(OC(=O)CCl)CC1 ORJQHLZQXNJZQL-UHFFFAOYSA-N 0.000 description 1
- QTLRCBWYAHFIAY-UHFFFAOYSA-N (1-methylpiperidin-4-yl) 2-chloroacetate;hydrochloride Chemical compound Cl.CN1CCC(OC(=O)CCl)CC1 QTLRCBWYAHFIAY-UHFFFAOYSA-N 0.000 description 1
- GXCKTGDXEMXGHB-UHFFFAOYSA-N (1-prop-2-ynylpiperidin-4-yl) 2-chloroacetate Chemical compound ClCC(=O)OC1CCN(CC#C)CC1 GXCKTGDXEMXGHB-UHFFFAOYSA-N 0.000 description 1
- SUIBBXBEUCIBSA-UHFFFAOYSA-N (1-prop-2-ynylpiperidin-4-yl) 2-chloroacetate hydrochloride Chemical compound Cl.ClCC(=O)OC1CCN(CC#C)CC1 SUIBBXBEUCIBSA-UHFFFAOYSA-N 0.000 description 1
- KYGMSTKBHJVPJK-UHFFFAOYSA-N 1-(2-phenylethyl)piperidin-4-ol Chemical compound C1CC(O)CCN1CCC1=CC=CC=C1 KYGMSTKBHJVPJK-UHFFFAOYSA-N 0.000 description 1
- BPPZXJZYCOETDA-UHFFFAOYSA-N 1-benzylpiperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC=C1 BPPZXJZYCOETDA-UHFFFAOYSA-N 0.000 description 1
- RLKMOPWWGZKHOP-UHFFFAOYSA-N 1-butylpiperidin-4-ol Chemical compound CCCCN1CCC(O)CC1 RLKMOPWWGZKHOP-UHFFFAOYSA-N 0.000 description 1
- AHOJTPZHHMJMCW-UHFFFAOYSA-N 1-ethylpiperidin-4-ol Chemical compound CCN1CCC(O)CC1 AHOJTPZHHMJMCW-UHFFFAOYSA-N 0.000 description 1
- JVMCZMQYJIRKRV-UHFFFAOYSA-N 1-methyl-4-phenylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CC=CC=C1 JVMCZMQYJIRKRV-UHFFFAOYSA-N 0.000 description 1
- BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-UHFFFAOYSA-N 0.000 description 1
- CEUZTHSDJADUSJ-UHFFFAOYSA-N 1-prop-2-ynylpiperidin-4-ol Chemical compound OC1CCN(CC#C)CC1 CEUZTHSDJADUSJ-UHFFFAOYSA-N 0.000 description 1
- RGUIKQRAZCQMBM-UHFFFAOYSA-N 2-[[8-(trifluoromethyl)quinolin-4-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 RGUIKQRAZCQMBM-UHFFFAOYSA-N 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 241000208680 Hamamelis mollis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 206010061216 Infarction Diseases 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KUJXAEXIHCYQRX-UHFFFAOYSA-N [1-[2-(4-nitrophenyl)ethyl]piperidin-4-yl] 2-chloroacetate;hydrochloride Chemical compound Cl.C1=CC([N+](=O)[O-])=CC=C1CCN1CCC(OC(=O)CCl)CC1 KUJXAEXIHCYQRX-UHFFFAOYSA-N 0.000 description 1
- UPCKDNAOTOCEJO-UHFFFAOYSA-N [2-(1-benzylpiperidin-4-yl)oxy-2-oxoethyl] 2-[[8-(trifluoromethyl)quinolin-4-yl]amino]benzoate Chemical compound C1=CN=C2C(C(F)(F)F)=CC=CC2=C1NC1=CC=CC=C1C(=O)OCC(=O)OC(CC1)CCN1CC1=CC=CC=C1 UPCKDNAOTOCEJO-UHFFFAOYSA-N 0.000 description 1
- KSAMZNUOVWDJAO-UHFFFAOYSA-N [2-(1-methyl-4-phenylpiperidin-4-yl)oxy-2-oxoethyl] 2-[[8-(trifluoromethyl)quinolin-4-yl]amino]benzoate Chemical compound C1CN(C)CCC1(C=1C=CC=CC=1)OC(=O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 KSAMZNUOVWDJAO-UHFFFAOYSA-N 0.000 description 1
- LNRHOEPINOFRPT-UHFFFAOYSA-N [2-(1-methylpiperidin-4-yl)oxy-2-oxoethyl] 2-[[7-(trifluoromethyl)quinolin-4-yl]amino]benzoate Chemical compound C1CN(C)CCC1OC(=O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(C(F)(F)F)=CC=C12 LNRHOEPINOFRPT-UHFFFAOYSA-N 0.000 description 1
- BJCWECRJPYQDGK-UHFFFAOYSA-N [2-oxo-2-(1-phenacylpiperidin-4-yl)oxyethyl] 2-[(7-chloroquinolin-4-yl)amino]benzoate Chemical compound C=1C=NC2=CC(Cl)=CC=C2C=1NC1=CC=CC=C1C(=O)OCC(=O)OC(CC1)CCN1CC(=O)C1=CC=CC=C1 BJCWECRJPYQDGK-UHFFFAOYSA-N 0.000 description 1
- NDUGXSQEVKPTFA-UHFFFAOYSA-N [2-oxo-2-(1-prop-2-enylpiperidin-4-yl)oxyethyl] 2-[(7-chloroquinolin-4-yl)amino]benzoate Chemical compound C=1C=NC2=CC(Cl)=CC=C2C=1NC1=CC=CC=C1C(=O)OCC(=O)OC1CCN(CC=C)CC1 NDUGXSQEVKPTFA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940118846 witch hazel Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Biological Depolymerization Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8134398 | 1981-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO823659L true NO823659L (no) | 1983-05-16 |
Family
ID=10525904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO823659A NO823659L (no) | 1981-11-14 | 1982-11-03 | Fremgangsmaate for fremstilling av antraniloyl-oksyalkanoater |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4482561A (it) |
| EP (1) | EP0079740B1 (it) |
| JP (1) | JPS58135882A (it) |
| AT (1) | ATE16490T1 (it) |
| AU (1) | AU9045382A (it) |
| CA (1) | CA1193260A (it) |
| DE (1) | DE3242196A1 (it) |
| DK (1) | DK485282A (it) |
| ES (1) | ES8404685A1 (it) |
| FI (1) | FI823723L (it) |
| GR (1) | GR77367B (it) |
| HU (1) | HU188224B (it) |
| IL (1) | IL67194A (it) |
| IT (1) | IT1196425B (it) |
| NL (1) | NL8204384A (it) |
| NO (1) | NO823659L (it) |
| NZ (1) | NZ202320A (it) |
| PT (1) | PT75834B (it) |
| ZA (1) | ZA828234B (it) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3742580C1 (de) * | 1987-12-16 | 1989-05-11 | Schaper & Bruemmer Gmbh | Verwendung des alpha,alpha-Diphenyl-alpha-(3-carboxy-propionyloxy)-essigsaeure-4-(N-methylpiperidyl)-esters zur Behandlung hypertoner Funktionszustaende im Bereich der Harnblase |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE589546A (it) * | 1959-04-15 | |||
| FR6103M (it) * | 1967-02-22 | 1968-06-10 | ||
| FR6195M (it) * | 1967-04-11 | 1968-07-22 | ||
| FR2434808A1 (fr) * | 1978-09-01 | 1980-03-28 | Science Union & Cie | Nouveaux esters du methyl-1 piperidinol-4, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| FR2467846A1 (fr) * | 1979-10-22 | 1981-04-30 | Dufour J C | Nouveaux b hydroxy esters de piperidyle |
-
1982
- 1982-10-29 NZ NZ202320A patent/NZ202320A/en unknown
- 1982-11-01 FI FI823723A patent/FI823723L/fi not_active Application Discontinuation
- 1982-11-02 DK DK485282A patent/DK485282A/da not_active Application Discontinuation
- 1982-11-03 ES ES517062A patent/ES8404685A1/es not_active Expired
- 1982-11-03 NO NO823659A patent/NO823659L/no unknown
- 1982-11-04 GR GR69725A patent/GR77367B/el unknown
- 1982-11-08 EP EP82305928A patent/EP0079740B1/en not_active Expired
- 1982-11-08 AT AT82305928T patent/ATE16490T1/de active
- 1982-11-08 IL IL67194A patent/IL67194A/xx unknown
- 1982-11-10 ZA ZA828234A patent/ZA828234B/xx unknown
- 1982-11-10 JP JP57198314A patent/JPS58135882A/ja active Pending
- 1982-11-11 PT PT75834A patent/PT75834B/pt unknown
- 1982-11-11 IT IT24204/82A patent/IT1196425B/it active
- 1982-11-12 CA CA000415439A patent/CA1193260A/en not_active Expired
- 1982-11-12 AU AU90453/82A patent/AU9045382A/en not_active Abandoned
- 1982-11-12 US US06/441,093 patent/US4482561A/en not_active Expired - Fee Related
- 1982-11-12 NL NL8204384A patent/NL8204384A/nl not_active Application Discontinuation
- 1982-11-12 HU HU823650A patent/HU188224B/hu unknown
- 1982-11-15 DE DE19823242196 patent/DE3242196A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| HU188224B (en) | 1986-03-28 |
| ATE16490T1 (de) | 1985-11-15 |
| US4482561A (en) | 1984-11-13 |
| ZA828234B (en) | 1983-09-28 |
| ES517062A0 (es) | 1984-05-16 |
| NL8204384A (nl) | 1983-06-01 |
| JPS58135882A (ja) | 1983-08-12 |
| EP0079740B1 (en) | 1985-11-13 |
| NZ202320A (en) | 1985-05-31 |
| IT1196425B (it) | 1988-11-16 |
| FI823723L (fi) | 1983-05-15 |
| CA1193260A (en) | 1985-09-10 |
| AU9045382A (en) | 1983-05-19 |
| DK485282A (da) | 1983-05-15 |
| GR77367B (it) | 1984-09-11 |
| DE3242196A1 (de) | 1983-05-26 |
| IL67194A0 (en) | 1983-03-31 |
| EP0079740A1 (en) | 1983-05-25 |
| IL67194A (en) | 1986-04-29 |
| FI823723A0 (fi) | 1982-11-01 |
| PT75834A (en) | 1982-12-01 |
| PT75834B (en) | 1985-11-12 |
| IT8224204A0 (it) | 1982-11-11 |
| ES8404685A1 (es) | 1984-05-16 |
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