SK8052000A3 - Process for the preparation of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine - Google Patents
Process for the preparation of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine Download PDFInfo
- Publication number
- SK8052000A3 SK8052000A3 SK805-2000A SK8052000A SK8052000A3 SK 8052000 A3 SK8052000 A3 SK 8052000A3 SK 8052000 A SK8052000 A SK 8052000A SK 8052000 A3 SK8052000 A3 SK 8052000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- propoxyphenoxy
- ethyl
- amine
- carried out
- isopropylmethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims description 7
- NUZYBIKIXLKGKN-UHFFFAOYSA-N n-methyl-n-[2-(3-propoxyphenoxy)ethyl]propan-2-amine Chemical compound CCCOC1=CC=CC(OCCN(C)C(C)C)=C1 NUZYBIKIXLKGKN-UHFFFAOYSA-N 0.000 title abstract description 6
- -1 isopropylmethyl- [2- (3-n-propoxyphenoxy) ethyl] amine Chemical class 0.000 claims description 45
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000003444 phase transfer catalyst Substances 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 235000011181 potassium carbonates Nutrition 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
- 230000007704 transition Effects 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 235000017550 sodium carbonate Nutrition 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000008118 PEG 6000 Substances 0.000 claims description 2
- 229920002584 Polyethylene Glycol 6000 Polymers 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- MAPRDOKILZKGDP-UHFFFAOYSA-N bromo-chloro-iodomethanesulfonic acid Chemical group OS(=O)(=O)C(Cl)(Br)I MAPRDOKILZKGDP-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000008098 formaldehyde solution Substances 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- SWZLTTGLPJCPPM-UHFFFAOYSA-N 2-(3-propoxyphenoxy)ethanol Chemical compound CCCOC1=CC=CC(OCCO)=C1 SWZLTTGLPJCPPM-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 4
- YYMPIPSWQOGUME-UHFFFAOYSA-N 3-propoxyphenol Chemical compound CCCOC1=CC=CC(O)=C1 YYMPIPSWQOGUME-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- XCKPIQCKBIUGBT-UHFFFAOYSA-N 1-(2-bromoethoxy)-3-propoxybenzene Chemical compound CCCOC1=CC=CC(OCCBr)=C1 XCKPIQCKBIUGBT-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 231100000219 mutagenic Toxicity 0.000 description 2
- 230000003505 mutagenic effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UGHCXAZHFPONAE-UHFFFAOYSA-N ethanesulfonic acid;4-methylbenzenesulfonic acid Chemical compound CCS(O)(=O)=O.CC1=CC=C(S(O)(=O)=O)C=C1 UGHCXAZHFPONAE-UHFFFAOYSA-N 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000000699 topical effect Effects 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Anesthesiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9704834A SE9704834D0 (sv) | 1997-12-22 | 1997-12-22 | New process |
| PCT/SE1998/002315 WO1999032430A1 (en) | 1997-12-22 | 1998-12-15 | Process for the preparation of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK8052000A3 true SK8052000A3 (en) | 2001-02-12 |
Family
ID=20409537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK805-2000A SK8052000A3 (en) | 1997-12-22 | 1998-12-15 | Process for the preparation of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1045826A1 (et) |
| JP (1) | JP2001526253A (et) |
| KR (1) | KR20010024790A (et) |
| CN (1) | CN1283177A (et) |
| AR (1) | AR017198A1 (et) |
| AU (1) | AU1989199A (et) |
| BR (1) | BR9814377A (et) |
| CA (1) | CA2314988A1 (et) |
| EE (1) | EE200000369A (et) |
| HU (1) | HUP0100616A2 (et) |
| ID (1) | ID27591A (et) |
| IL (1) | IL136825A0 (et) |
| IS (1) | IS5523A (et) |
| NO (1) | NO20002944L (et) |
| PL (1) | PL341438A1 (et) |
| SE (1) | SE9704834D0 (et) |
| SK (1) | SK8052000A3 (et) |
| TR (1) | TR200001976T2 (et) |
| TW (1) | TW436474B (et) |
| WO (1) | WO1999032430A1 (et) |
| ZA (1) | ZA9811238B (et) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2714639A1 (en) * | 2011-05-26 | 2014-04-09 | Solvay Specialty Polymers Italy S.p.A. | Hydro-fluorocompounds |
| JP6247992B2 (ja) * | 2014-04-17 | 2017-12-13 | 株式会社ダイセル | ハロゲン化合物の製造方法 |
| JP6635999B2 (ja) * | 2017-10-13 | 2020-01-29 | 株式会社ダイセル | カリウム塩の製造方法、及びカリウム塩 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL90704A (en) * | 1989-06-21 | 1994-10-07 | Makhteshim Chem Works Ltd | Method for the preparation of N-N-) 2,4,6-trichlorophenoxy (environmentally reliable ethylene) |
| AR004691A1 (es) * | 1995-10-27 | 1999-03-10 | Astrazeneca Ab | Nuevos derivados de [3-alcoxi-fenoxi-)-etil]-dialquilamina, una composicion farmaceutica que los comprende, su uso como anestesicos locales y unprocedimiento para su preparacion |
-
1997
- 1997-12-22 SE SE9704834A patent/SE9704834D0/xx unknown
-
1998
- 1998-12-08 ZA ZA9811238A patent/ZA9811238B/xx unknown
- 1998-12-09 TW TW087120435A patent/TW436474B/zh not_active IP Right Cessation
- 1998-12-09 AR ARP980106239A patent/AR017198A1/es not_active Application Discontinuation
- 1998-12-15 WO PCT/SE1998/002315 patent/WO1999032430A1/en not_active Ceased
- 1998-12-15 BR BR9814377-8A patent/BR9814377A/pt not_active IP Right Cessation
- 1998-12-15 AU AU19891/99A patent/AU1989199A/en not_active Abandoned
- 1998-12-15 EE EEP200000369A patent/EE200000369A/et unknown
- 1998-12-15 SK SK805-2000A patent/SK8052000A3/sk unknown
- 1998-12-15 ID IDW20001192A patent/ID27591A/id unknown
- 1998-12-15 TR TR2000/01976T patent/TR200001976T2/xx unknown
- 1998-12-15 CA CA002314988A patent/CA2314988A1/en not_active Abandoned
- 1998-12-15 EP EP98964599A patent/EP1045826A1/en not_active Ceased
- 1998-12-15 IL IL13682598A patent/IL136825A0/xx unknown
- 1998-12-15 PL PL98341438A patent/PL341438A1/xx not_active Application Discontinuation
- 1998-12-15 CN CN98812528A patent/CN1283177A/zh active Pending
- 1998-12-15 HU HU0100616A patent/HUP0100616A2/hu unknown
- 1998-12-15 JP JP2000525367A patent/JP2001526253A/ja active Pending
- 1998-12-15 KR KR1020007006880A patent/KR20010024790A/ko not_active Withdrawn
-
2000
- 2000-06-07 IS IS5523A patent/IS5523A/is unknown
- 2000-06-08 NO NO20002944A patent/NO20002944L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2314988A1 (en) | 1999-07-01 |
| PL341438A1 (en) | 2001-04-09 |
| NO20002944D0 (no) | 2000-06-08 |
| TW436474B (en) | 2001-05-28 |
| HUP0100616A2 (hu) | 2002-05-29 |
| AU1989199A (en) | 1999-07-12 |
| EE200000369A (et) | 2001-12-17 |
| EP1045826A1 (en) | 2000-10-25 |
| JP2001526253A (ja) | 2001-12-18 |
| ZA9811238B (en) | 1999-06-22 |
| IS5523A (is) | 2000-06-07 |
| IL136825A0 (en) | 2001-06-14 |
| SE9704834D0 (sv) | 1997-12-22 |
| AR017198A1 (es) | 2001-08-22 |
| CN1283177A (zh) | 2001-02-07 |
| KR20010024790A (ko) | 2001-03-26 |
| TR200001976T2 (tr) | 2000-11-21 |
| ID27591A (id) | 2001-04-12 |
| NO20002944L (no) | 2000-06-08 |
| WO1999032430A1 (en) | 1999-07-01 |
| BR9814377A (pt) | 2000-10-10 |
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