NO751238L - - Google Patents
Info
- Publication number
- NO751238L NO751238L NO751238A NO751238A NO751238L NO 751238 L NO751238 L NO 751238L NO 751238 A NO751238 A NO 751238A NO 751238 A NO751238 A NO 751238A NO 751238 L NO751238 L NO 751238L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- benzamide
- ethoxy
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003152 propanolamines Chemical class 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- -1 oxazolidine compound Chemical class 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- CVQWYCCXJPYZQI-UHFFFAOYSA-N 4-(2-chloroethoxy)benzamide Chemical compound NC(=O)C1=CC=C(OCCCl)C=C1 CVQWYCCXJPYZQI-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 150000002917 oxazolidines Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 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
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WPLHSDOLOPJHHX-UHFFFAOYSA-N 2-(2-chloroethoxy)benzamide Chemical compound NC(=O)C1=CC=CC=C1OCCCl WPLHSDOLOPJHHX-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- FYMBZEYAAOFXFH-UHFFFAOYSA-N 4-[2-[[2-hydroxy-3-(2-methoxyphenoxy)propyl]amino]ethoxy]benzamide Chemical compound C(N)(=O)C1=CC=C(OCCNCC(COC2=C(C=CC=C2)OC)O)C=C1 FYMBZEYAAOFXFH-UHFFFAOYSA-N 0.000 description 1
- SKQDKFOTIPJUSV-UHFFFAOYSA-N 4-[2-[[2-hydroxy-3-(2-methylphenoxy)propyl]amino]ethoxy]benzamide Chemical compound CC1=CC=CC=C1OCC(O)CNCCOC1=CC=C(C(N)=O)C=C1 SKQDKFOTIPJUSV-UHFFFAOYSA-N 0.000 description 1
- ZATQSCRQPQXBEG-UHFFFAOYSA-N 4-[2-[[2-hydroxy-3-(2-methylphenoxy)propyl]amino]ethoxy]benzamide;hydrochloride Chemical compound Cl.CC1=CC=CC=C1OCC(O)CNCCOC1=CC=C(C(N)=O)C=C1 ZATQSCRQPQXBEG-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- GXGGAMQHXKHZSA-UHFFFAOYSA-N 5-[(2-methylphenoxy)methyl]-1,3-oxazolidin-2-one Chemical compound CC1=CC=CC=C1OCC1OC(=O)NC1 GXGGAMQHXKHZSA-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZMNSRFNUONFLSP-UHFFFAOYSA-N mephenoxalone Chemical compound COC1=CC=CC=C1OCC1OC(=O)NC1 ZMNSRFNUONFLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (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 |
|---|---|---|---|
| GB1603074A GB1435276A (en) | 1974-04-10 | 1974-04-10 | Oxazolidines and conversion to propanolamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO751238L true NO751238L (fr) | 1975-10-13 |
Family
ID=10069885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO751238A NO751238L (fr) | 1974-04-10 | 1975-04-09 |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS50148324A (fr) |
| AT (1) | ATA268375A (fr) |
| BE (1) | BE827473A (fr) |
| CH (1) | CH603609A5 (fr) |
| DD (2) | DD121635A5 (fr) |
| DE (1) | DE2514553A1 (fr) |
| DK (1) | DK152575A (fr) |
| EG (1) | EG11656A (fr) |
| ES (1) | ES436499A1 (fr) |
| FI (1) | FI751079A (fr) |
| FR (1) | FR2272979B3 (fr) |
| GB (1) | GB1435276A (fr) |
| HU (2) | HU169604B (fr) |
| IE (1) | IE40974B1 (fr) |
| IL (1) | IL46993A0 (fr) |
| IN (1) | IN141076B (fr) |
| LU (1) | LU72240A1 (fr) |
| NL (1) | NL7504214A (fr) |
| NO (1) | NO751238L (fr) |
| PH (1) | PH11695A (fr) |
| PL (2) | PL99021B1 (fr) |
| RO (1) | RO69153A (fr) |
| SE (1) | SE7503565L (fr) |
| ZA (1) | ZA752266B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH635573A5 (en) * | 1977-03-24 | 1983-04-15 | Sandoz Ag | Process for preparing novel 1,2-dihydroxypropane derivatives |
| DD150456A5 (de) * | 1979-03-01 | 1981-09-02 | Ciba Geigy Ag | Verfahren zur herstellung von derivaten des 3-amino-1,2-propandiols |
-
1974
- 1974-04-10 GB GB1603074A patent/GB1435276A/en not_active Expired
-
1975
- 1975-03-26 SE SE7503565A patent/SE7503565L/xx not_active Application Discontinuation
- 1975-04-01 IL IL46993A patent/IL46993A0/xx unknown
- 1975-04-02 BE BE155017A patent/BE827473A/fr unknown
- 1975-04-03 IN IN681/CAL/75A patent/IN141076B/en unknown
- 1975-04-03 DE DE19752514553 patent/DE2514553A1/de active Pending
- 1975-04-04 PH PH17018A patent/PH11695A/en unknown
- 1975-04-05 EG EG196A patent/EG11656A/xx active
- 1975-04-08 FR FR7510897A patent/FR2272979B3/fr not_active Expired
- 1975-04-08 LU LU72240A patent/LU72240A1/xx unknown
- 1975-04-09 ZA ZA00752266A patent/ZA752266B/xx unknown
- 1975-04-09 NL NL7504214A patent/NL7504214A/xx unknown
- 1975-04-09 CH CH452075A patent/CH603609A5/xx not_active IP Right Cessation
- 1975-04-09 DD DD185328A patent/DD121635A5/xx unknown
- 1975-04-09 NO NO751238A patent/NO751238L/no unknown
- 1975-04-09 IE IE805/75A patent/IE40974B1/xx unknown
- 1975-04-09 PL PL1975179460A patent/PL99021B1/pl unknown
- 1975-04-09 HU HUPI461A patent/HU169604B/hu unknown
- 1975-04-09 AT AT268375A patent/ATA268375A/de not_active Application Discontinuation
- 1975-04-09 DK DK152575A patent/DK152575A/da not_active IP Right Cessation
- 1975-04-09 HU HU75PI00000520A patent/HU172061B/hu unknown
- 1975-04-09 JP JP50043141A patent/JPS50148324A/ja active Pending
- 1975-04-09 DD DD191668A patent/DD123989A5/xx unknown
- 1975-04-09 PL PL1975195855A patent/PL97545B1/pl unknown
- 1975-04-10 RO RO7581955A patent/RO69153A/fr unknown
- 1975-04-10 ES ES436499A patent/ES436499A1/es not_active Expired
- 1975-04-10 FI FI751079A patent/FI751079A/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL99021B1 (pl) | 1978-06-30 |
| CH603609A5 (fr) | 1978-08-31 |
| NL7504214A (nl) | 1975-10-14 |
| IN141076B (fr) | 1977-01-15 |
| ZA752266B (en) | 1976-03-31 |
| GB1435276A (en) | 1976-05-12 |
| IL46993A0 (en) | 1975-06-25 |
| HU169604B (fr) | 1976-12-28 |
| DD121635A5 (fr) | 1976-08-12 |
| ATA268375A (de) | 1976-09-15 |
| BE827473A (fr) | 1975-10-02 |
| LU72240A1 (fr) | 1977-02-02 |
| JPS50148324A (fr) | 1975-11-27 |
| ES436499A1 (es) | 1977-02-01 |
| IE40974B1 (en) | 1979-09-26 |
| PH11695A (en) | 1978-05-24 |
| DE2514553A1 (de) | 1975-10-23 |
| SE7503565L (sv) | 1975-10-13 |
| FR2272979B3 (fr) | 1977-12-16 |
| EG11656A (en) | 1977-11-30 |
| IE40974L (en) | 1975-10-10 |
| DD123989A5 (fr) | 1977-01-26 |
| HU172061B (hu) | 1978-05-28 |
| RO69153A (fr) | 1982-09-09 |
| AU7982775A (en) | 1976-10-07 |
| FI751079A (fr) | 1975-10-11 |
| PL97545B1 (pl) | 1978-03-30 |
| DK152575A (fr) | 1975-10-11 |
| FR2272979A1 (fr) | 1975-12-26 |
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