HUP0100616A2 - Eljárás izopropil-metil-[2-(3-propoxi-fenoxi)-etil]-amin előállítására - Google Patents

Eljárás izopropil-metil-[2-(3-propoxi-fenoxi)-etil]-amin előállítására Download PDF

Info

Publication number: HUP0100616A2
Authority: HU; Hungary
Prior art keywords: ethyl; amine; propoxyphenoxy; isopropylmethyl; process according
Prior art date: 1997-12-22

Application number

HU0100616A

Other languages

English (en)

Hungarian (hu)

Inventor

Ulf Larsson

Original Assignee

Astrazeneca Ab,

Priority date (The priority date 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 date listed.)

1997-12-22

Filing date

1998-12-15

Publication date

2002-05-29

1998-12-15 Application filed by Astrazeneca Ab, filed Critical Astrazeneca Ab,

2002-05-29 Publication of HUP0100616A2 publication Critical patent/HUP0100616A2/hu

Links

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 claims abstract description 39
238000000034 method Methods 0.000 title claims abstract description 38
238000002360 preparation method Methods 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 16
-1 sulfonate ester Chemical class 0.000 claims abstract description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 13
239000003960 organic solvent Substances 0.000 claims abstract description 8
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 7
239000007864 aqueous solution Substances 0.000 claims abstract description 6
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims abstract description 5
239000007791 liquid phase Substances 0.000 claims abstract description 5
238000003408 phase transfer catalysis Methods 0.000 claims abstract description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 11
239000011541 reaction mixture Substances 0.000 claims description 9
239000003444 phase transfer catalyst Substances 0.000 claims description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
235000011181 potassium carbonates Nutrition 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 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
239000007787 solid Substances 0.000 claims description 4
AJCVAONAXVRAIP-UHFFFAOYSA-N n-[2-(3-propoxyphenoxy)ethyl]propan-2-amine Chemical compound CCCOC1=CC=CC(OCCNC(C)C)=C1 AJCVAONAXVRAIP-UHFFFAOYSA-N 0.000 claims description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Chemical group 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000011736 potassium bicarbonate Substances 0.000 claims description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
235000017550 sodium carbonate Nutrition 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
229910052763 palladium Inorganic materials 0.000 claims 2
239000003085 diluting agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
SWZLTTGLPJCPPM-UHFFFAOYSA-N 2-(3-propoxyphenoxy)ethanol Chemical compound CCCOC1=CC=CC(OCCO)=C1 SWZLTTGLPJCPPM-UHFFFAOYSA-N 0.000 abstract description 9
238000000746 purification Methods 0.000 abstract description 7
YYMPIPSWQOGUME-UHFFFAOYSA-N 3-propoxyphenol Chemical compound CCCOC1=CC=CC(O)=C1 YYMPIPSWQOGUME-UHFFFAOYSA-N 0.000 abstract description 4
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract description 4
238000004519 manufacturing process Methods 0.000 abstract description 3
238000002425 crystallisation Methods 0.000 abstract description 2
230000008025 crystallization Effects 0.000 abstract description 2
239000013067 intermediate product Substances 0.000 abstract description 2
239000003513 alkali Substances 0.000 abstract 1
150000004820 halides Chemical class 0.000 abstract 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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 15
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000012074 organic phase Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 8
239000012071 phase Substances 0.000 description 8
235000011007 phosphoric acid Nutrition 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
DHTWNVFGIQXZEM-UHFFFAOYSA-N 2-(3-propoxyphenoxy)ethyl methanesulfonate Chemical compound CCCOC1=CC=CC(OCCOS(C)(=O)=O)=C1 DHTWNVFGIQXZEM-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
CZDRVARQTVNKNO-UHFFFAOYSA-N n-methyl-n-[2-(3-propoxyphenoxy)ethyl]propan-2-amine;phosphoric acid Chemical compound OP(O)(O)=O.CCCOC1=CC=CC(OCCN(C)C(C)C)=C1 CZDRVARQTVNKNO-UHFFFAOYSA-N 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 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
239000000047 product Substances 0.000 description 2
239000008213 purified water Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
XCKPIQCKBIUGBT-UHFFFAOYSA-N 1-(2-bromoethoxy)-3-propoxybenzene Chemical compound CCCOC1=CC=CC(OCCBr)=C1 XCKPIQCKBIUGBT-UHFFFAOYSA-N 0.000 description 1
PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
206010064571 Gene mutation Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001345 alkine derivatives 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
229910052799 carbon Inorganic materials 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 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
229920001223 polyethylene glycol Polymers 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 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
- 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)

HU0100616A 1997-12-22 1998-12-15 Eljárás izopropil-metil-[2-(3-propoxi-fenoxi)-etil]-amin előállítására HUP0100616A2 (hu)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE9704834A SE9704834D0 (sv)	1997-12-22	1997-12-22	New process

Publications (1)

Publication Number	Publication Date
HUP0100616A2 true HUP0100616A2 (hu)	2002-05-29

Family

ID=20409537

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU0100616A HUP0100616A2 (hu)	1997-12-22	1998-12-15	Eljárás izopropil-metil-[2-(3-propoxi-fenoxi)-etil]-amin előállítására

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)	NO20002944D0 (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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 BR BR9814377-8A patent/BR9814377A/pt not_active IP Right Cessation
- 1998-12-15 TR TR2000/01976T patent/TR200001976T2/xx unknown
- 1998-12-15 SK SK805-2000A patent/SK8052000A3/sk unknown
- 1998-12-15 CN CN98812528A patent/CN1283177A/zh active Pending
- 1998-12-15 JP JP2000525367A patent/JP2001526253A/ja active Pending
- 1998-12-15 KR KR1020007006880A patent/KR20010024790A/ko not_active Withdrawn
- 1998-12-15 IL IL13682598A patent/IL136825A0/xx unknown
- 1998-12-15 AU AU19891/99A patent/AU1989199A/en not_active Abandoned
- 1998-12-15 HU HU0100616A patent/HUP0100616A2/hu unknown
- 1998-12-15 ID IDW20001192A patent/ID27591A/id unknown
- 1998-12-15 WO PCT/SE1998/002315 patent/WO1999032430A1/en not_active Ceased
- 1998-12-15 CA CA002314988A patent/CA2314988A1/en not_active Abandoned
- 1998-12-15 EE EEP200000369A patent/EE200000369A/et unknown
- 1998-12-15 PL PL98341438A patent/PL341438A1/xx not_active Application Discontinuation
- 1998-12-15 EP EP98964599A patent/EP1045826A1/en not_active Ceased
2000
- 2000-06-07 IS IS5523A patent/IS5523A/is unknown
- 2000-06-08 NO NO20002944A patent/NO20002944D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CA2314988A1 (en)	1999-07-01
TR200001976T2 (tr)	2000-11-21
SE9704834D0 (sv)	1997-12-22
CN1283177A (zh)	2001-02-07
WO1999032430A1 (en)	1999-07-01
AR017198A1 (es)	2001-08-22
SK8052000A3 (en)	2001-02-12
ZA9811238B (en)	1999-06-22
NO20002944L (no)	2000-06-08
NO20002944D0 (no)	2000-06-08
EE200000369A (et)	2001-12-17
JP2001526253A (ja)	2001-12-18
IL136825A0 (en)	2001-06-14
PL341438A1 (en)	2001-04-09
ID27591A (id)	2001-04-12
AU1989199A (en)	1999-07-12
KR20010024790A (ko)	2001-03-26
IS5523A (is)	2000-06-07
TW436474B (en)	2001-05-28
BR9814377A (pt)	2000-10-10
EP1045826A1 (en)	2000-10-25

Publication	Publication Date	Title
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