NO742960L - - Google Patents
Info
- Publication number
- NO742960L NO742960L NO742960A NO742960A NO742960L NO 742960 L NO742960 L NO 742960L NO 742960 A NO742960 A NO 742960A NO 742960 A NO742960 A NO 742960A NO 742960 L NO742960 L NO 742960L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- aziridine
- hydroxy
- propyl
- Prior art date
Links
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- QXSAKPUBHTZHKW-UHFFFAOYSA-N 4-hydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 claims description 8
- -1 N-substituted aziridine Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical group CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000003152 propanolamines Chemical class 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- HOYCXZRZVKWLOO-UHFFFAOYSA-N 1-(aziridin-1-yl)-3-(2-methylphenoxy)propan-2-ol Chemical compound OC(CN1CC1)COC1=C(C=CC=C1)C HOYCXZRZVKWLOO-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 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 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000006308 propyl amino group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000013074 reference sample Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- ZYPHHKSLTMTACH-UHFFFAOYSA-N 1-(aziridin-1-yl)-3-(2-methoxyphenoxy)propan-2-ol Chemical compound OC(CN1CC1)COC1=C(C=CC=C1)OC ZYPHHKSLTMTACH-UHFFFAOYSA-N 0.000 description 1
- KFUSXMDYOPXKKT-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OCC1OC1 KFUSXMDYOPXKKT-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005138 alkoxysulfonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/10—Radicals substituted by singly bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3916273A GB1413911A (en) | 1973-08-18 | 1973-08-18 | Preparation of propanolamine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO742960L true NO742960L (es) | 1975-02-19 |
Family
ID=10408018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO742960A NO742960L (es) | 1973-08-18 | 1974-08-16 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3911008A (es) |
| JP (1) | JPS5052035A (es) |
| AT (1) | AT331781B (es) |
| BE (1) | BE818579A (es) |
| CH (1) | CH583172A5 (es) |
| DD (1) | DD115654A5 (es) |
| DE (1) | DE2438077A1 (es) |
| DK (1) | DK135943B (es) |
| ES (1) | ES429336A1 (es) |
| FI (1) | FI237074A (es) |
| FR (1) | FR2240916B1 (es) |
| GB (1) | GB1413911A (es) |
| IE (1) | IE40438B1 (es) |
| IL (1) | IL45276A0 (es) |
| LU (1) | LU70743A1 (es) |
| NL (1) | NL7410604A (es) |
| NO (1) | NO742960L (es) |
| RO (1) | RO68383A (es) |
| SE (1) | SE7409899L (es) |
| ZA (1) | ZA744439B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4165384A (en) * | 1974-11-01 | 1979-08-21 | Aktiebolaget Hassle | Amide substituted phenoxy propanol amines |
| US4391826A (en) * | 1978-07-03 | 1983-07-05 | Eli Lilly And Company | Phenethanolamines, compositions containing the same, and method for effecting weight control |
| US4845127A (en) * | 1978-07-03 | 1989-07-04 | Eli Lilly And Company | Phenethanolamines, compositions containing the same and method for effecting weight control |
| ATE2265T1 (de) * | 1979-10-25 | 1983-02-15 | Beecham Group Plc | Sekundaere amine, ihre herstellung und verwendung in pharmazeutischen zusammensetzungen. |
| DE3162756D1 (en) * | 1980-05-22 | 1984-04-26 | Beecham Group Plc | Arylethanolamine derivatives, their preparation and use in pharmaceutical compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3852468A (en) * | 1967-02-27 | 1974-12-03 | Ici Ltd | Alkanolamine derivatives as {62 -adrenergic blocking agents |
| GB1269775A (en) * | 1968-07-18 | 1972-04-06 | Ici Ltd | Alkanolamine derivatives |
| DE1957706C3 (de) * | 1968-11-18 | 1978-06-29 | Pfizer Corp., Colon (Panama) | Kernsubstituierte 3-Phenoxy-l-phenoxyalkylamino-propan-2-ole und Arzneimittel auf deren Basis |
-
1973
- 1973-08-18 GB GB3916273A patent/GB1413911A/en not_active Expired
-
1974
- 1974-07-10 ZA ZA00744439A patent/ZA744439B/xx unknown
- 1974-07-16 IL IL45276A patent/IL45276A0/xx unknown
- 1974-07-31 SE SE7409899A patent/SE7409899L/xx unknown
- 1974-08-07 DE DE2438077A patent/DE2438077A1/de not_active Withdrawn
- 1974-08-07 JP JP49090681A patent/JPS5052035A/ja active Pending
- 1974-08-07 NL NL7410604A patent/NL7410604A/xx not_active Application Discontinuation
- 1974-08-07 BE BE147369A patent/BE818579A/xx unknown
- 1974-08-07 IE IE1656/74A patent/IE40438B1/xx unknown
- 1974-08-07 RO RO7400079690A patent/RO68383A/ro unknown
- 1974-08-08 FI FI2370/74A patent/FI237074A/fi unknown
- 1974-08-12 DK DK429574AA patent/DK135943B/da unknown
- 1974-08-13 DD DD180470A patent/DD115654A5/xx unknown
- 1974-08-14 CH CH1108074A patent/CH583172A5/xx not_active IP Right Cessation
- 1974-08-14 AT AT667174A patent/AT331781B/de not_active IP Right Cessation
- 1974-08-14 FR FR7428370A patent/FR2240916B1/fr not_active Expired
- 1974-08-15 US US497625A patent/US3911008A/en not_active Expired - Lifetime
- 1974-08-16 NO NO742960A patent/NO742960L/no unknown
- 1974-08-16 LU LU70743A patent/LU70743A1/xx unknown
- 1974-08-17 ES ES429336A patent/ES429336A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA667174A (de) | 1975-12-15 |
| BE818579A (fr) | 1975-02-07 |
| FR2240916B1 (es) | 1979-08-03 |
| DK429574A (es) | 1975-04-28 |
| AT331781B (de) | 1976-08-25 |
| FI237074A (es) | 1975-02-19 |
| SE7409899L (es) | 1975-02-19 |
| IL45276A0 (en) | 1974-10-22 |
| CH583172A5 (es) | 1976-12-31 |
| DK135943B (da) | 1977-07-18 |
| LU70743A1 (es) | 1976-08-19 |
| NL7410604A (nl) | 1975-02-20 |
| US3911008A (en) | 1975-10-07 |
| JPS5052035A (es) | 1975-05-09 |
| IE40438L (en) | 1975-02-18 |
| DE2438077A1 (de) | 1975-03-20 |
| GB1413911A (en) | 1975-11-12 |
| RO68383A (fr) | 1979-07-15 |
| ZA744439B (en) | 1975-07-30 |
| DK135943C (es) | 1977-12-19 |
| DD115654A5 (es) | 1975-10-12 |
| ES429336A1 (es) | 1976-10-01 |
| FR2240916A1 (es) | 1975-03-14 |
| IE40438B1 (en) | 1979-06-06 |
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