NO310614B1 - Nye [(3-alkoksyfenoksy)-etyl]-dialkylaminderivater, farmasöytisk preparat, anvendelse av derivatene til fremstillingav lokalanestetika, og fremgangsmåte for deres fremstilling - Google Patents
Nye [(3-alkoksyfenoksy)-etyl]-dialkylaminderivater, farmasöytisk preparat, anvendelse av derivatene til fremstillingav lokalanestetika, og fremgangsmåte for deres fremstilling Download PDFInfo
- Publication number
- NO310614B1 NO310614B1 NO19981825A NO981825A NO310614B1 NO 310614 B1 NO310614 B1 NO 310614B1 NO 19981825 A NO19981825 A NO 19981825A NO 981825 A NO981825 A NO 981825A NO 310614 B1 NO310614 B1 NO 310614B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- preparation
- pharmaceutically acceptable
- acceptable salt
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 239000003589 local anesthetic agent Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- 229960005015 local anesthetics Drugs 0.000 title description 8
- 125000005265 dialkylamine group Chemical group 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 230000003444 anaesthetic effect Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 230000036407 pain Effects 0.000 claims description 6
- 230000000699 topical effect Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- NUZYBIKIXLKGKN-UHFFFAOYSA-N n-methyl-n-[2-(3-propoxyphenoxy)ethyl]propan-2-amine Chemical group CCCOC1=CC=CC(OCCN(C)C(C)C)=C1 NUZYBIKIXLKGKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 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 description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 230000036592 analgesia Effects 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- -1 local anaesthetics) Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 206010002091 Anaesthesia Diseases 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 230000037005 anaesthesia Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- IOOCVIRRKFNHEL-UHFFFAOYSA-N 3-pentoxyphenol Chemical compound CCCCCOC1=CC=CC(O)=C1 IOOCVIRRKFNHEL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229940035674 anesthetics Drugs 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- STBPTJBXUNWORN-UHFFFAOYSA-N n,n-diethyl-2-(3-propoxyphenoxy)ethanamine Chemical compound CCCOC1=CC=CC(OCCN(CC)CC)=C1 STBPTJBXUNWORN-UHFFFAOYSA-N 0.000 description 2
- CEYGESXGJKWCIX-UHFFFAOYSA-N n-[2-(3-butoxyphenoxy)ethyl]-n-ethylpropan-2-amine Chemical compound CCCCOC1=CC=CC(OCCN(CC)C(C)C)=C1 CEYGESXGJKWCIX-UHFFFAOYSA-N 0.000 description 2
- PEKNLAYQOAFBJI-UHFFFAOYSA-N n-[2-(3-butoxyphenoxy)ethyl]-n-methylpropan-2-amine Chemical compound CCCCOC1=CC=CC(OCCN(C)C(C)C)=C1 PEKNLAYQOAFBJI-UHFFFAOYSA-N 0.000 description 2
- HTZHMHUPICTOEX-UHFFFAOYSA-N n-[2-(3-butoxyphenoxy)ethyl]-n-propan-2-ylpropan-2-amine Chemical compound CCCCOC1=CC=CC(OCCN(C(C)C)C(C)C)=C1 HTZHMHUPICTOEX-UHFFFAOYSA-N 0.000 description 2
- YEXPSDFZHXGBQY-UHFFFAOYSA-N n-ethyl-n-[2-(3-pentoxyphenoxy)ethyl]propan-2-amine Chemical compound CCCCCOC1=CC=CC(OCCN(CC)C(C)C)=C1 YEXPSDFZHXGBQY-UHFFFAOYSA-N 0.000 description 2
- SNVBNYIAYXLQBS-UHFFFAOYSA-N n-ethyl-n-[2-(3-propoxyphenoxy)ethyl]propan-2-amine Chemical compound CCCOC1=CC=CC(OCCN(CC)C(C)C)=C1 SNVBNYIAYXLQBS-UHFFFAOYSA-N 0.000 description 2
- QKMGNUHPMISNEB-UHFFFAOYSA-N n-propan-2-yl-n-[2-(3-propoxyphenoxy)ethyl]propan-2-amine Chemical compound CCCOC1=CC=CC(OCCN(C(C)C)C(C)C)=C1 QKMGNUHPMISNEB-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 238000002691 topical anesthesia Methods 0.000 description 2
- QMGAMPRXFICLLM-UHFFFAOYSA-N 1-(2-bromoethoxy)-3-butoxybenzene Chemical compound CCCCOC1=CC=CC(OCCBr)=C1 QMGAMPRXFICLLM-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- LHYNOYNIFPOFLF-UHFFFAOYSA-N 2-(2,6-dimethoxyphenoxy)-n,n-dimethylethanamine Chemical compound COC1=CC=CC(OC)=C1OCCN(C)C LHYNOYNIFPOFLF-UHFFFAOYSA-N 0.000 description 1
- VGIJZDWQVCXVNL-UHFFFAOYSA-N 3-butoxyphenol Chemical compound CCCCOC1=CC=CC(O)=C1 VGIJZDWQVCXVNL-UHFFFAOYSA-N 0.000 description 1
- YYMPIPSWQOGUME-UHFFFAOYSA-N 3-propoxyphenol Chemical compound CCCOC1=CC=CC(O)=C1 YYMPIPSWQOGUME-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- NNWPEJLXVHZECD-UHFFFAOYSA-N n-[2-(3-pentoxyphenoxy)ethyl]-n-propan-2-ylpropan-2-amine Chemical compound CCCCCOC1=CC=CC(OCCN(C(C)C)C(C)C)=C1 NNWPEJLXVHZECD-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- HPUOAJPGWQQRNT-UHFFFAOYSA-N pentoxybenzene Chemical compound CCCCCOC1=CC=CC=C1 HPUOAJPGWQQRNT-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
-
- 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]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9503798A SE9503798D0 (sv) | 1995-10-27 | 1995-10-27 | New anaesthetic componds |
| SE9600329A SE9600329D0 (sv) | 1996-01-30 | 1996-01-30 | New anaesthetic compounds |
| PCT/SE1996/001361 WO1997015548A1 (en) | 1995-10-27 | 1996-10-23 | New [(3-alkoxy-phenoxy)-ethyl]-dialkylamine derivatives and their use as local anaesthetics |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO981825L NO981825L (no) | 1998-04-23 |
| NO981825D0 NO981825D0 (no) | 1998-04-23 |
| NO310614B1 true NO310614B1 (no) | 2001-07-30 |
Family
ID=26662410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19981825A NO310614B1 (no) | 1995-10-27 | 1998-04-23 | Nye [(3-alkoksyfenoksy)-etyl]-dialkylaminderivater, farmasöytisk preparat, anvendelse av derivatene til fremstillingav lokalanestetika, og fremgangsmåte for deres fremstilling |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6310252B1 (es) |
| EP (1) | EP0858445B1 (es) |
| JP (1) | JP4101877B2 (es) |
| KR (1) | KR100460652B1 (es) |
| CN (1) | CN1113856C (es) |
| AR (1) | AR004691A1 (es) |
| AT (1) | ATE215061T1 (es) |
| AU (1) | AU704635B2 (es) |
| BR (1) | BR9611234A (es) |
| CA (1) | CA2233489C (es) |
| CZ (1) | CZ124198A3 (es) |
| DE (1) | DE69620213T2 (es) |
| DK (1) | DK0858445T3 (es) |
| EE (1) | EE03963B1 (es) |
| ES (1) | ES2174113T3 (es) |
| HK (1) | HK1009437A1 (es) |
| HU (1) | HUP9901212A3 (es) |
| IL (1) | IL123916A (es) |
| IS (1) | IS1932B (es) |
| MY (1) | MY132329A (es) |
| NO (1) | NO310614B1 (es) |
| NZ (1) | NZ320757A (es) |
| PL (1) | PL186783B1 (es) |
| PT (1) | PT858445E (es) |
| SI (1) | SI0858445T1 (es) |
| SK (1) | SK282757B6 (es) |
| TR (1) | TR199800714T2 (es) |
| TW (1) | TW448142B (es) |
| UA (1) | UA59347C2 (es) |
| WO (1) | WO1997015548A1 (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6432986B2 (en) | 1997-07-21 | 2002-08-13 | Bruce H. Levin | Compositions, kits, and methods for inhibiting cerebral neurovascular disorders and muscular headaches |
| US7799337B2 (en) | 1997-07-21 | 2010-09-21 | Levin Bruce H | Method for directed intranasal administration of a composition |
| SE9704031D0 (sv) * | 1997-11-05 | 1997-11-05 | Astra Ab | Novel formulation |
| SE9704770D0 (sv) * | 1997-12-19 | 1997-12-19 | Astra Ab | New use |
| SE9704834D0 (sv) * | 1997-12-22 | 1997-12-22 | Astra Ab | New process |
| SE9704835D0 (sv) | 1997-12-22 | 1997-12-22 | Astra Ab | New compound |
| JP2000302737A (ja) * | 1999-04-16 | 2000-10-31 | Shiseido Co Ltd | 二置換ベンゼン誘導体 |
| US8473062B2 (en) | 2008-05-01 | 2013-06-25 | Autonomic Technologies, Inc. | Method and device for the treatment of headache |
| US8412336B2 (en) | 2008-12-29 | 2013-04-02 | Autonomic Technologies, Inc. | Integrated delivery and visualization tool for a neuromodulation system |
| US9012477B2 (en) | 2009-01-06 | 2015-04-21 | Nuvo Research Inc. | Method of treating neuropathic pain |
| US9320908B2 (en) | 2009-01-15 | 2016-04-26 | Autonomic Technologies, Inc. | Approval per use implanted neurostimulator |
| US8494641B2 (en) | 2009-04-22 | 2013-07-23 | Autonomic Technologies, Inc. | Implantable neurostimulator with integral hermetic electronic enclosure, circuit substrate, monolithic feed-through, lead assembly and anchoring mechanism |
| BR112012017554B8 (pt) | 2010-01-14 | 2021-05-25 | Crescita Therapeutics Inc | formulações de anestésicas locais formadoras de sólido para controle da dor |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1173136A (fr) | 1955-11-16 | 1959-02-20 | Rech S Et Tech Appliquees | Dérivés tertio-amino-alcoxylés du benzène et leur procédé de préparation |
| CH380746A (de) | 1958-11-06 | 1964-08-15 | Ciba Geigy | Verfahren zur Herstellung neuer sekundärer Amine |
| GB1027611A (en) | 1962-01-04 | 1966-04-27 | May & Baker Ltd | Phenoxy- and phenylthio-alkylamines and acid addition salts thereof |
| US3205136A (en) * | 1962-12-24 | 1965-09-07 | Smith Kline French Lab | Antidepressant phenyloxyalkylamines |
| DE3233828A1 (de) | 1982-09-11 | 1984-03-15 | Basf Ag, 6700 Ludwigshafen | Aryloxyalkylamine, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
-
1996
- 1996-10-14 AR ARP960104736A patent/AR004691A1/es unknown
- 1996-10-15 TW TW085112594A patent/TW448142B/zh not_active IP Right Cessation
- 1996-10-23 DE DE69620213T patent/DE69620213T2/de not_active Expired - Lifetime
- 1996-10-23 SI SI9630469T patent/SI0858445T1/xx unknown
- 1996-10-23 EP EP96935752A patent/EP0858445B1/en not_active Expired - Lifetime
- 1996-10-23 WO PCT/SE1996/001361 patent/WO1997015548A1/en not_active Application Discontinuation
- 1996-10-23 AU AU73561/96A patent/AU704635B2/en not_active Ceased
- 1996-10-23 PT PT96935752T patent/PT858445E/pt unknown
- 1996-10-23 CA CA002233489A patent/CA2233489C/en not_active Expired - Fee Related
- 1996-10-23 SK SK553-98A patent/SK282757B6/sk unknown
- 1996-10-23 BR BR9611234A patent/BR9611234A/pt not_active IP Right Cessation
- 1996-10-23 UA UA98042083A patent/UA59347C2/uk unknown
- 1996-10-23 KR KR10-1998-0703023A patent/KR100460652B1/ko not_active IP Right Cessation
- 1996-10-23 HU HU9901212A patent/HUP9901212A3/hu unknown
- 1996-10-23 ES ES96935752T patent/ES2174113T3/es not_active Expired - Lifetime
- 1996-10-23 JP JP51653997A patent/JP4101877B2/ja not_active Expired - Fee Related
- 1996-10-23 CN CN96197845A patent/CN1113856C/zh not_active Expired - Fee Related
- 1996-10-23 CZ CZ981241A patent/CZ124198A3/cs unknown
- 1996-10-23 TR TR1998/00714T patent/TR199800714T2/xx unknown
- 1996-10-23 IL IL12391696A patent/IL123916A/en not_active IP Right Cessation
- 1996-10-23 NZ NZ320757A patent/NZ320757A/xx not_active IP Right Cessation
- 1996-10-23 EE EE9800088A patent/EE03963B1/xx not_active IP Right Cessation
- 1996-10-23 US US08/776,620 patent/US6310252B1/en not_active Expired - Fee Related
- 1996-10-23 DK DK96935752T patent/DK0858445T3/da active
- 1996-10-23 AT AT96935752T patent/ATE215061T1/de active
- 1996-10-23 PL PL96326425A patent/PL186783B1/pl not_active IP Right Cessation
- 1996-10-25 MY MYPI96004455A patent/MY132329A/en unknown
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1998
- 1998-03-25 IS IS4702A patent/IS1932B/is unknown
- 1998-04-23 NO NO19981825A patent/NO310614B1/no not_active IP Right Cessation
- 1998-09-01 HK HK98110334A patent/HK1009437A1/xx not_active IP Right Cessation
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