FI65986C - (s)-1-aryloxi-2-propanolderivat anvaendbara som mellanprodukter vid framstaellning av (s)-1-aryloxi-3-amino-2-propanolderivat - Google Patents

(s)-1-aryloxi-2-propanolderivat anvaendbara som mellanprodukter vid framstaellning av (s)-1-aryloxi-3-amino-2-propanolderivat Download PDF

Info

Publication number: FI65986C
Authority: FI; Finland
Prior art keywords: group; carbon atoms; naphthyl; amino; phenyl
Prior art date: 1973-11-09

Application number

FI3242/74A

Other languages

English (en)

Finnish (fi)

Other versions

FI65986B (fi

FI324274A (da

Inventor

Howard Tucker

Original Assignee

Ici Ltd

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.)

1973-11-09

Filing date

1974-11-07

Publication date

1984-08-10

1974-11-07 Application filed by Ici Ltd filed Critical Ici Ltd

1975-05-10 Publication of FI324274A publication Critical patent/FI324274A/fi

1984-04-30 Application granted granted Critical

1984-04-30 Publication of FI65986B publication Critical patent/FI65986B/fi

1984-08-10 Publication of FI65986C publication Critical patent/FI65986C/fi

Links

-1 hydroxy, amino, hydroxyiminomethyl Chemical group 0.000 claims description 72
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000005133 alkynyloxy group Chemical group 0.000 claims description 3
125000004103 aminoalkyl group Chemical group 0.000 claims description 3
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 3
125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000005159 cyanoalkoxy group Chemical group 0.000 claims description 3
125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 3
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000001769 aryl amino group Chemical group 0.000 claims description 2
125000005110 aryl thio group Chemical group 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
239000000047 product Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 2
206010008631 Cholera Diseases 0.000 claims 1
125000004450 alkenylene group Chemical group 0.000 claims 1
125000004104 aryloxy group Chemical group 0.000 claims 1
239000006227 byproduct Substances 0.000 claims 1
239000003086 colorant Substances 0.000 claims 1
230000001404 mediated effect Effects 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
150000001875 compounds Chemical class 0.000 description 26
239000000203 mixture Substances 0.000 description 18
239000000243 solution Substances 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
239000007858 starting material Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
238000000034 method Methods 0.000 description 6
239000007787 solid Substances 0.000 description 5
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
YBPAYPRLUDCSEY-UHFFFAOYSA-N p-hydroxyphenylacetoamide Natural products NC(=O)CC1=CC=C(O)C=C1 YBPAYPRLUDCSEY-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000004593 Epoxy Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
150000002009 diols Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
239000010410 layer Substances 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
DTDBWQMKXKHERX-LBPRGKRZSA-N [(2S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxy]propyl] 4-methylbenzenesulfonate Chemical compound C(C)(C)(C)OC[C@@H](COS(=O)(=O)C1=CC=C(C=C1)C)O DTDBWQMKXKHERX-LBPRGKRZSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
HBMUWOSOGHUWSS-UHFFFAOYSA-N (2-hydroxy-3-phenylmethoxypropyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC(O)COCC1=CC=CC=C1 HBMUWOSOGHUWSS-UHFFFAOYSA-N 0.000 description 1
JPWDLYMEUNBLIR-ZCFIWIBFSA-N (2r)-3-[(2-methylpropan-2-yl)oxy]propane-1,2-diol Chemical compound CC(C)(C)OC[C@H](O)CO JPWDLYMEUNBLIR-ZCFIWIBFSA-N 0.000 description 1
ASVZARXJSBYDCV-GFCCVEGCSA-N 2-[(2S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxy]propoxy]benzonitrile Chemical compound C(#N)C1=C(OC[C@H](COC(C)(C)C)O)C=CC=C1 ASVZARXJSBYDCV-GFCCVEGCSA-N 0.000 description 1
YTTFGUYTPJYRBQ-LBPRGKRZSA-N 2-[(2s)-2-hydroxy-3-(propan-2-ylamino)propoxy]benzonitrile Chemical compound CC(C)NC[C@H](O)COC1=CC=CC=C1C#N YTTFGUYTPJYRBQ-LBPRGKRZSA-N 0.000 description 1
CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
KMNGNJCCNKBBCI-UHFFFAOYSA-N Cl.C1(=CC=CC2=CC=CC=C12)C(C)(C)Cl Chemical compound Cl.C1(=CC=CC2=CC=CC=C12)C(C)(C)Cl KMNGNJCCNKBBCI-UHFFFAOYSA-N 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000012267 brine Substances 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
230000005415 magnetization Effects 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
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 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Epoxy Compounds (AREA)

FI3242/74A 1973-11-09 1974-11-07 (s)-1-aryloxi-2-propanolderivat anvaendbara som mellanprodukter vid framstaellning av (s)-1-aryloxi-3-amino-2-propanolderivat FI65986C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB5207773		1973-11-09
GB5207773A GB1458392A (en)	1973-11-09	1973-11-09	Optically-active 1-aryloxy-2,3-epoxypropane derivatives

Publications (3)

Publication Number	Publication Date
FI324274A FI324274A (da)	1975-05-10
FI65986B FI65986B (fi)	1984-04-30
FI65986C true FI65986C (fi)	1984-08-10

Family

ID=10462547

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI3242/74A FI65986C (fi)	1973-11-09	1974-11-07	(s)-1-aryloxi-2-propanolderivat anvaendbara som mellanprodukter vid framstaellning av (s)-1-aryloxi-3-amino-2-propanolderivat

Country Status (10)

Country	Link
US (1)	US4085136A (da)
JP (1)	JPS617412B2 (da)
CH (1)	CH611866A5 (da)
DE (1)	DE2453324A1 (da)
DK (1)	DK155085C (da)
FI (1)	FI65986C (da)
FR (1)	FR2250752B1 (da)
GB (1)	GB1458392A (da)
NO (1)	NO145056C (da)
SE (1)	SE425971B (da)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2330383A1 (fr) *	1975-11-06	1977-06-03	Synthelabo	Nouveaux ethers de phenols substitues, leurs sels, leur preparation et les medicaments qui les renferment
DE2839475A1 (de) *	1978-09-11	1980-03-20	Dolorgiet Arzneimittelfabrik	Isopropylamin-verbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
US4342783A (en) *	1980-06-30	1982-08-03	Synthelabo	Anti-glaucoma agent
US4396629A (en) *	1980-12-29	1983-08-02	Sterling Drug Inc.	Compositions, processes and method
DE3319027A1 (de) *	1983-05-26	1984-11-29	Boehringer Mannheim Gmbh, 6800 Mannheim	Verfahren zur herstellung von optisch aktiven carbazol-derivaten, neue r- und s-carbazol-derivate, sowie arzneimittel, die diese verbindungen enthalten
JPS6087237A (ja) *	1983-10-19	1985-05-16	Toyo Sutoufuaa Chem:Kk	光学活性なケトンの製造方法
JPS60184039A (ja) *	1984-03-01	1985-09-19	Toyo Sutoufuaa Chem:Kk	光学活性なケトンの製造方法
GB8419683D0 (en) *	1984-08-02	1984-09-05	Erba Farmitalia	3-substituted derivatives of 1-amino-2-hydroxy-propane
US4956284A (en) *	1985-02-13	1990-09-11	Gist-Brocades N.V.	Process for producing 4-(2-methoxyethyl)-phenyl-glycidyl ether and/or metoprolol
AU589594B2 (en) *	1985-02-13	1989-10-19	Gist-Brocades N.V.	Process for the preparation of arylglycidyl ethers and 3-substituted 1-alkylamino-2-propanlos
GB8503666D0 (en) *	1985-02-13	1985-03-13	Shell Int Research	Producing 4-(2-methoxyethyl)-phenylglycidyl ether
US4945182A (en) *	1985-12-24	1990-07-31	Merck & Co., Inc.	Oculoselective beta-blockers
GB8607312D0 (en) *	1986-03-25	1986-04-30	Ici Plc	Therapeutic agents
GB8618324D0 (en) *	1986-07-28	1986-09-03	Shell Int Research	Phenylacetate/atenolol
US5223646A (en) *	1989-12-27	1993-06-29	Daiso Company, Ltd.	Process for producing optically active atenolol and intermediate thereof
JPH0674243B2 (ja) *	1989-12-27	1994-09-21	ダイソー株式会社	光学純度の高い光学活性アテノロール塩及びアテノロールの製法
SE9000207L (sv) *	1990-01-22	1991-07-23	Nobel Chemicals Ab	Laekemedel samt anvaendningen av detsamma
SE468211B (sv) *	1990-01-22	1992-11-23	Nobel Chemicals Ab	Flerstegsfoerfarande foer framstaellning av homokirala aminer
US6946566B2 (en)	2002-07-31	2005-09-20	Daiso Co., Ltd.	Process for preparation of optically active halogeno hydroxypropyl compound and glycidyl compound
US6982349B1 (en)	2003-10-31	2006-01-03	Emcure Pharmaceuticals Limited	Process for producing atenolol of high optical purity

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1069343A (en) *	1963-09-10	1967-05-17	Ici Ltd	Propanolamine derivatives
US3494939A (en) *	1964-03-09	1970-02-10	Minnesota Mining & Mfg	Glycidoxy - bisnuclear - phenolic ethers of oxa-substituted aliphatic diols and triols
US3686320A (en) *	1965-03-25	1972-08-22	Fisons Pharmaceuticals Ltd	Bis-phenoxy compounds
GB1136919A (en) *	1965-06-16	1968-12-18	Ici Ltd	Amines
DE1668055B2 (de) *	1967-03-10	1973-09-06	Farbwerke Hoechst AG, vormals Mei ster Lucius & Bruning, 6000 Frankfurt	Basisch substituierte cyclopentylphenolaether, deren salze mit physiologisch vertraeglichen saeuren und verfahren zu deren herstellung
BE755071A (fr) *	1969-09-17	1971-02-22	Warner Lambert Pharmaceutical	Procede de resolution de la dl-5-/3-(terbutylamino)-2- hydroxy-propoxy/-3,4-dihydro-1(2h) naphtalenone
GB1410513A (en)	1971-10-27	1975-10-15	Syntex Inc	3-thiazol-2-oxy-propane derivatives

1973
- 1973-11-09 GB GB5207773A patent/GB1458392A/en not_active Expired
1974
- 1974-11-07 DK DK581474A patent/DK155085C/da active
- 1974-11-07 FI FI3242/74A patent/FI65986C/fi active
- 1974-11-07 NO NO744023A patent/NO145056C/no unknown
- 1974-11-07 SE SE7414017A patent/SE425971B/xx not_active IP Right Cessation
- 1974-11-08 CH CH1499674A patent/CH611866A5/xx not_active IP Right Cessation
- 1974-11-08 FR FR7437127A patent/FR2250752B1/fr not_active Expired
- 1974-11-08 JP JP49128841A patent/JPS617412B2/ja not_active Expired
- 1974-11-11 DE DE19742453324 patent/DE2453324A1/de active Granted
1976
- 1976-06-09 US US05/694,323 patent/US4085136A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NO744023L (da)	1975-06-02
DK155085C (da)	1989-06-26
FR2250752A1 (da)	1975-06-06
JPS5077331A (da)	1975-06-24
SE425971B (sv)	1982-11-29
FI65986B (fi)	1984-04-30
FR2250752B1 (da)	1979-03-16
NO145056B (no)	1981-09-21
FI324274A (da)	1975-05-10
CH611866A5 (da)	1979-06-29
DE2453324A1 (de)	1975-05-22
US4085136A (en)	1978-04-18
JPS617412B2 (da)	1986-03-06
SE7414017L (da)	1975-05-12
DK155085B (da)	1989-02-06
DK581474A (da)	1975-07-07
NO145056C (no)	1982-01-04
GB1458392A (en)	1976-12-15
DE2453324C2 (da)	1989-07-06

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