FI62060C - Foerfarande foer framstaellning av beta-blockerande substituerad 2-hydroxi-3-(2-acyl-4-ureido-fenoxi)-propylaminderivat - Google Patents
Foerfarande foer framstaellning av beta-blockerande substituerad 2-hydroxi-3-(2-acyl-4-ureido-fenoxi)-propylaminderivat Download PDFInfo
- Publication number
- FI62060C FI62060C FI3612/74A FI361274A FI62060C FI 62060 C FI62060 C FI 62060C FI 3612/74 A FI3612/74 A FI 3612/74A FI 361274 A FI361274 A FI 361274A FI 62060 C FI62060 C FI 62060C
- Authority
- FI
- Finland
- Prior art keywords
- group
- formula
- hydroxy
- phenyl
- propoxy
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 63
- -1 ethyleneoxyethylene group Chemical group 0.000 claims description 27
- 239000002585 base Substances 0.000 claims description 23
- 239000004202 carbamide Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
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- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
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- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 150000003672 ureas Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
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- 239000003937 drug carrier Substances 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
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- 239000007858 starting material Substances 0.000 description 35
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- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
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- 238000002474 experimental method Methods 0.000 description 5
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- 238000001953 recrystallisation Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000002876 beta blocker Substances 0.000 description 4
- 229940097320 beta blocking agent Drugs 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 4
- 238000001665 trituration Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DXVQSHRBALIFBC-UHFFFAOYSA-N 3-phenoxypropan-1-amine Chemical class NCCCOC1=CC=CC=C1 DXVQSHRBALIFBC-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000003929 acidic solution Substances 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
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- 239000000126 substance Substances 0.000 description 3
- IMHPUHMLCNLANZ-UHFFFAOYSA-N 1-[benzyl(propan-2-yl)amino]-3-chloropropan-2-ol Chemical compound ClCC(O)CN(C(C)C)CC1=CC=CC=C1 IMHPUHMLCNLANZ-UHFFFAOYSA-N 0.000 description 2
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
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- 230000035484 reaction time Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/38—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
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)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT1066673A AT334385B (de) | 1973-12-20 | 1973-12-20 | Verfahren zur herstellung von neuen phenoxypropylaminderivaten und deren salzen |
| AT1066673 | 1973-12-20 | ||
| AT926674 | 1974-11-19 | ||
| AT926674A AT335464B (de) | 1974-11-19 | 1974-11-19 | Verfahren zur herstellung von neuen 3-(p-ureidophenoxy)-2-hydroxy-aminopropanen sowie deren saureadditionssalzen |
| AT930874 | 1974-11-20 | ||
| AT930874A AT335465B (de) | 1974-11-20 | 1974-11-20 | Verfahren zur herstellung von neuen 3-(p-ureidophenoxy)-2-hydroxy-aminopropanen sowie deren saureadditionssalzen |
| AT943674 | 1974-11-25 | ||
| AT943674A AT335467B (de) | 1974-11-25 | 1974-11-25 | Verfahren zur herstellung von neuen 3-(p-ureidophenoxy)-2-hydroxy-aminopropanen sowie deren saureadditionssalzen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI361274A7 FI361274A7 (enrdf_load_stackoverflow) | 1975-06-21 |
| FI62060B FI62060B (fi) | 1982-07-30 |
| FI62060C true FI62060C (fi) | 1982-11-10 |
Family
ID=27422270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3612/74A FI62060C (fi) | 1973-12-20 | 1974-12-13 | Foerfarande foer framstaellning av beta-blockerande substituerad 2-hydroxi-3-(2-acyl-4-ureido-fenoxi)-propylaminderivat |
Country Status (7)
| Country | Link |
|---|---|
| DE (1) | DE2458624C3 (enrdf_load_stackoverflow) |
| DK (1) | DK136816B (enrdf_load_stackoverflow) |
| FI (1) | FI62060C (enrdf_load_stackoverflow) |
| HU (1) | HU170678B (enrdf_load_stackoverflow) |
| NL (2) | NL179281C (enrdf_load_stackoverflow) |
| NO (1) | NO149134C (enrdf_load_stackoverflow) |
| SE (1) | SE420089B (enrdf_load_stackoverflow) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4470965A (en) * | 1982-10-27 | 1984-09-11 | Usv Pharmaceutical Corporation | Celiprolol for the treatment of glaucoma |
| EP0117089B1 (en) * | 1983-02-03 | 1988-12-14 | The Regents Of The University Of California | Beta-adrenergic antagonist compounds and derivatives of beta-adrenergic antagonists |
| US4687873A (en) * | 1983-02-03 | 1987-08-18 | The Regents Of The University Of California | Derivatives of β-adrenergic antagonists |
| DE3410380A1 (de) * | 1984-03-21 | 1985-10-10 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | S(-)-celiprolol, dessen pharmazeutisch vertraegliche salze, verfahren zu dessen herstellung, verwendung in der therapie und pharmazeutische zubereitungen |
| AT380232B (de) * | 1984-03-27 | 1986-04-25 | Chemie Linz Ag | Verfahren zur herstellung von neuen s(-)-3-(3-acetyl-4-(3-tert. butylamino-2hydroxypropoxy)-phenyl)-1,1-diaethylharnstoff und dessen pharmazeutisch vertraeglichen saeureadditionssalzen |
| DE3544172A1 (de) * | 1985-12-13 | 1987-06-19 | Lentia Gmbh | Neue kristalline salze von aryloxy-propanolaminen, verfahren zu ihrer herstellung und ihre verwendung |
| US20010018446A1 (en) | 1999-09-23 | 2001-08-30 | G.D. Searle & Co. | Substituted N-Aliphatic-N-Aromatictertiary-Heteroalkylamines useful for inhibiting cholesteryl ester transfer protein activity |
| US20040259912A1 (en) * | 2001-09-28 | 2004-12-23 | Takahiro Matsumoto | Benzine derivatives, process for preparing the same and use thereof |
-
1974
- 1974-12-09 HU HUCE1031A patent/HU170678B/hu unknown
- 1974-12-11 DE DE2458624A patent/DE2458624C3/de not_active Expired
- 1974-12-13 FI FI3612/74A patent/FI62060C/fi active
- 1974-12-17 SE SE7415832A patent/SE420089B/xx not_active IP Right Cessation
- 1974-12-18 NO NO744569A patent/NO149134C/no unknown
- 1974-12-20 NL NLAANVRAGE7416685,A patent/NL179281C/xx not_active IP Right Cessation
- 1974-12-20 DK DK671074AA patent/DK136816B/da not_active IP Right Cessation
-
1993
- 1993-03-25 NL NL930024C patent/NL930024I2/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2458624C3 (de) | 1979-09-20 |
| SE7415832L (enrdf_load_stackoverflow) | 1975-06-23 |
| DE2458624A1 (de) | 1975-07-03 |
| DK136816B (da) | 1977-11-28 |
| NL7416685A (nl) | 1975-06-24 |
| FI62060B (fi) | 1982-07-30 |
| DK671074A (enrdf_load_stackoverflow) | 1975-09-01 |
| NO149134C (no) | 1984-02-29 |
| NO744569L (enrdf_load_stackoverflow) | 1975-07-14 |
| NL930024I2 (nl) | 1993-10-01 |
| NL930024I1 (nl) | 1993-05-17 |
| DE2458624B2 (de) | 1979-01-25 |
| DK136816C (enrdf_load_stackoverflow) | 1978-05-08 |
| NL179281B (nl) | 1986-03-17 |
| NO149134B (no) | 1983-11-14 |
| HU170678B (enrdf_load_stackoverflow) | 1977-08-28 |
| SE420089B (sv) | 1981-09-14 |
| FI361274A7 (enrdf_load_stackoverflow) | 1975-06-21 |
| NL179281C (nl) | 1986-08-18 |
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