BE823616A - Preparation de la 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-t-butylaminoethyl) pyridine et composes intermediaires - Google Patents

Preparation de la 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-t-butylaminoethyl) pyridine et composes intermediaires

Info

Publication number: BE823616A
Authority: BE; Belgium
Prior art keywords: emi; formula; hydroxy; product; acid
Prior art date: 1973-12-26

Application number

BE1006340A

Other languages

English (en)

French (fr)

Inventor

S Nakanishi

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.)

1973-12-26

Filing date

1974-12-20

Publication date

1975-06-20

1974-12-20 Application filed filed Critical

1975-06-20 Publication of BE823616A publication Critical patent/BE823616A/fr

Links

150000001875 compounds Chemical class 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title description 4
VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical class CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 title description 2
238000006243 chemical reaction Methods 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 11
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 11
238000010992 reflux Methods 0.000 claims description 9
239000003054 catalyst Substances 0.000 claims description 8
229910052763 palladium Inorganic materials 0.000 claims description 6
238000005903 acid hydrolysis reaction Methods 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
-1 ketone acetal Chemical class 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
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
239000002994 raw material Substances 0.000 claims description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
241000219112 Cucumis Species 0.000 claims 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 claims 1
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims 1
235000012208 gluconic acid Nutrition 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
239000000047 product Substances 0.000 description 23
239000000203 mixture Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000725 suspension Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000012458 free base Substances 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
241000124008 Mammalia Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229940124630 bronchodilator Drugs 0.000 description 3
239000000168 bronchodilator agent Substances 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
238000000746 purification Methods 0.000 description 3
150000003222 pyridines Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000002452 interceptive effect Effects 0.000 description 2
239000010410 layer Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
PFCXYKDOJQERJW-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)pyridin-3-ol Chemical compound OCC1=CC=C(O)C(CO)=N1 PFCXYKDOJQERJW-UHFFFAOYSA-N 0.000 description 1
UUIMDJFBHNDZOW-UHFFFAOYSA-N 2-tert-butylpyridine Chemical class CC(C)(C)C1=CC=CC=N1 UUIMDJFBHNDZOW-UHFFFAOYSA-N 0.000 description 1
RBYURGMHFCPCNY-UHFFFAOYSA-N 6-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)pyridin-3-ol Chemical class NCC(O)C1=CC=C(O)C(CO)=N1 RBYURGMHFCPCNY-UHFFFAOYSA-N 0.000 description 1
ITLNNUNWMFNJRT-UHFFFAOYSA-N 6-(hydroxymethyl)-5-phenylmethoxypyridine-2-carbaldehyde Chemical compound OCC1=NC(C=O)=CC=C1OCC1=CC=CC=C1 ITLNNUNWMFNJRT-UHFFFAOYSA-N 0.000 description 1
IJAKLEKTAIWJTA-UHFFFAOYSA-N 6-[2-(tert-butylamino)-1-hydroxyethyl]pyridin-3-ol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C=N1 IJAKLEKTAIWJTA-UHFFFAOYSA-N 0.000 description 1
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000005703 Trimethylamine hydrochloride Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000048 adrenergic agonist Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
150000003944 halohydrins Chemical class 0.000 description 1
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BE1006340A 1973-12-26 1974-12-20 Preparation de la 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-t-butylaminoethyl) pyridine et composes intermediaires BE823616A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US42845173A	1973-12-26	1973-12-26

Publications (1)

Publication Number	Publication Date
BE823616A true BE823616A (fr)	1975-06-20

Family

ID=23698949

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE1006340A BE823616A (fr)	1973-12-26	1974-12-20	Preparation de la 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-t-butylaminoethyl) pyridine et composes intermediaires

Country Status (6)

Country	Link
JP (1)	JPS6056716B2 (de)
AT (1)	AT342589B (de)
BE (1)	BE823616A (de)
ES (1)	ES459322A1 (de)
PL (1)	PL110958B1 (de)
SU (1)	SU604486A3 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4011231A (en)	1975-10-03	1977-03-08	Pfizer Inc.	2-Phenyl-6-(1-hydroxy-2-t-butylaminoethyl)-4H-pyrido[3,2-d]-1,3-dioxin maleate and its use as an intermediate

1974
- 1974-12-18 AT AT1009874A patent/AT342589B/de not_active IP Right Cessation
- 1974-12-20 SU SU742100014A patent/SU604486A3/ru active
- 1974-12-20 BE BE1006340A patent/BE823616A/fr not_active IP Right Cessation
- 1974-12-21 PL PL21334974A patent/PL110958B1/pl unknown
1977
- 1977-05-31 ES ES459322A patent/ES459322A1/es not_active Expired
1985
- 1985-01-30 JP JP1636985A patent/JPS6056716B2/ja not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4011231A (en)	1975-10-03	1977-03-08	Pfizer Inc.	2-Phenyl-6-(1-hydroxy-2-t-butylaminoethyl)-4H-pyrido[3,2-d]-1,3-dioxin maleate and its use as an intermediate

Also Published As

Publication number	Publication date
PL110958B1 (en)	1980-08-30
ATA1009874A (de)	1977-08-15
JPS60185779A (ja)	1985-09-21
AT342589B (de)	1978-04-10
ES459322A1 (es)	1978-03-16
SU604486A3 (ru)	1978-04-25
JPS6056716B2 (ja)	1985-12-11

Legal Events

Date	Code	Title	Description
1993-06-28	CCPA	Application for a supplementary protection certificate	Free format text: 093C0125
1994-01-01	RE20	Patent expired	Owner name: PFIZER INC. Effective date: 19941220
1995-01-31	CCPV	Grant of a supplementary protection certificate	Free format text: 093C0125, EXPIRES 19990807
1999-08-07	CCRE	Expiry of a supplementary protection certificate	Free format text: 093C0125

Publication	Publication Date	Title
CH404664A (fr)	1965-12-31	Procédé de préparation de nouveaux composés hétérocycliques
CH648314A5 (fr)	1985-03-15	Procede de preparation de trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido(4,3-b)-indoles substitues en position 2 et composes permettant de les obtenir.
WO1979000319A1 (fr)	1979-06-14	Nouvelles indolo (2, 3-a) quinolizidines, leur preparation et leur utilisation therapeutique
EP0406112B1 (de)	1994-12-28	1-Benzhydrylazetidine, deren Herstellung und Verwendung als Zwischenprodukte zur Herstellung von Verbindungen mit antimikrobieller Wirkung
EP0376850B1 (de)	1993-03-03	Benzol-Derivate, ihre Herstellung und pharmazeutische Zusammensetzungen, die diese enthalten
BE1008622A3 (fr)	1996-06-04	Derives de l'epi-epibatidine.
CA1338637C (fr)	1996-10-08	Derives de la dihydro-1,4 pyridine, leurs procedes de preparation et les compositions pharmaceutiques les renfermant
BE823616A (fr)	1975-06-20	Preparation de la 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-t-butylaminoethyl) pyridine et composes intermediaires
FR2523977A1 (fr)	1983-09-30	Procede et composes intermediaires cles pour la preparation de la 19-norandrostenedione
BE854655A (fr)	1977-11-16	9-hydroxyhexahydrobenzo (c) quinoleines et intermediaires de synthese
US4031108A (en)	1977-06-21	2-Hydroxymethyl-3-benzyloxypyridine-6-epoxyethane
CH629821A5 (fr)	1982-05-14	Derives semi-synthetiques de l'oleandomycine et leur procede de preparation.
LU79767A1 (fr)	1980-01-22	Nouveaux 9-hydroxyhexahydrodibenzo(b,d)pyranes,leurs derives substitues en position 1,leur procede de preparation et medicament les contenant
US3948919A (en)	1976-04-06	2-Hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-t-butylaminoethyl)pyridine preparation and intermediate compounds
EP0002408A1 (de)	1979-06-13	Substituierte Phenoxyalkanole, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
BE1009080A4 (fr)	1996-11-05	Procede de preparation de l'epibatidine.
FR2621915A1 (fr)	1989-04-21	Produits chimiques intermediaires utilisables pour la preparation de certains agents anti-histaminiques h2 et leur procede de preparation
CH392508A (fr)	1965-05-31	Procédé de préparation d'esters de 3-phényl-3-pyrrolidinols
BE565010A (de)
BE884145R (fr)	1981-01-05	Composes indoliques nouveaux
CH641764A5 (fr)	1984-03-15	Sels d'imidoesters et procede de synthese de 2-naphtalene-ethanimidamide n,n'-disubstitues a partir desdits sels.
FR2494584A1 (fr)	1982-05-28	Medicaments constitues par de nouveaux 2-aminoethanols et leur procede de fabrication
BE635889A (de)
CH627446A5 (fr)	1982-01-15	Nouveaux derives de la benzamide.
CH408953A (fr)	1966-03-15	Procédé de préparation de nouveaux carbazates substitués

BE823616A - Preparation de la 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-t-butylaminoethyl) pyridine et composes intermediaires - Google Patents

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