FI62061C - Foerfarande foer framstaellning av nya beta-reseptorer blockerande 2-hydroxi-3-(2-oxiimino-4-ureidofenoxi)-propylaminderivat samt deras salter - Google Patents
Foerfarande foer framstaellning av nya beta-reseptorer blockerande 2-hydroxi-3-(2-oxiimino-4-ureidofenoxi)-propylaminderivat samt deras salter Download PDFInfo
- Publication number
- FI62061C FI62061C FI3657/74A FI365774A FI62061C FI 62061 C FI62061 C FI 62061C FI 3657/74 A FI3657/74 A FI 3657/74A FI 365774 A FI365774 A FI 365774A FI 62061 C FI62061 C FI 62061C
- Authority
- FI
- Finland
- Prior art keywords
- hydroxy
- propoxy
- phenyl
- tert
- butylamino
- Prior art date
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- -1 2-OXYIMINO-4-UREIDO-PHENOXY Chemical class 0.000 title claims description 14
- 101100148710 Clarkia breweri SAMT gene Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims description 5
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 1
- 241001024099 Olla Species 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 41
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000007858 starting material Substances 0.000 description 37
- 239000000047 product Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
- 238000002844 melting Methods 0.000 description 27
- 230000000694 effects Effects 0.000 description 25
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000013078 crystal Substances 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
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- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
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- 238000002474 experimental method Methods 0.000 description 7
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- 239000007864 aqueous solution Substances 0.000 description 6
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
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- 239000002876 beta blocker Substances 0.000 description 4
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- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
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- 125000004414 alkyl thio group Chemical group 0.000 description 2
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- 239000008103 glucose Substances 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
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- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
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- 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
- 150000003512 tertiary amines Chemical class 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
- 150000003672 ureas Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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 |
|---|---|---|---|
| AT1071873A AT334386B (de) | 1973-12-21 | 1973-12-21 | Verfahren zur herstellung von neuen phenoxypropylaminderivaten und deren salzen |
| AT1071873 | 1973-12-21 | ||
| 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 |
| AT939174 | 1974-11-22 | ||
| AT939174A AT335466B (de) | 1974-11-22 | 1974-11-22 | Verfahren zur herstellung von neuen 3-(p-ureidophenoxy)-2-hydroxy-aminopropanen und 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 |
|---|---|
| FI365774A7 FI365774A7 (enrdf_load_stackoverflow) | 1975-06-22 |
| FI62061B FI62061B (fi) | 1982-07-30 |
| FI62061C true FI62061C (fi) | 1982-11-10 |
Family
ID=27422272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3657/74A FI62061C (fi) | 1973-12-21 | 1974-12-17 | Foerfarande foer framstaellning av nya beta-reseptorer blockerande 2-hydroxi-3-(2-oxiimino-4-ureidofenoxi)-propylaminderivat samt deras salter |
Country Status (6)
| Country | Link |
|---|---|
| DE (1) | DE2458625C3 (enrdf_load_stackoverflow) |
| DK (1) | DK138985C (enrdf_load_stackoverflow) |
| FI (1) | FI62061C (enrdf_load_stackoverflow) |
| HU (1) | HU170677B (enrdf_load_stackoverflow) |
| NO (1) | NO149735C (enrdf_load_stackoverflow) |
| SE (1) | SE422790B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1974
- 1974-12-09 HU HUCE1030A patent/HU170677B/hu not_active IP Right Cessation
- 1974-12-11 DE DE2458625A patent/DE2458625C3/de not_active Expired
- 1974-12-16 NO NO744534A patent/NO149735C/no unknown
- 1974-12-17 SE SE7415833A patent/SE422790B/xx not_active IP Right Cessation
- 1974-12-17 FI FI3657/74A patent/FI62061C/fi active
- 1974-12-20 DK DK671174A patent/DK138985C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| NO149735B (no) | 1984-03-05 |
| DE2458625C3 (de) | 1981-04-23 |
| DK138985C (da) | 1979-04-30 |
| HU170677B (enrdf_load_stackoverflow) | 1977-08-28 |
| FI62061B (fi) | 1982-07-30 |
| SE422790B (sv) | 1982-03-29 |
| DK671174A (enrdf_load_stackoverflow) | 1975-08-25 |
| SE7415833L (enrdf_load_stackoverflow) | 1975-06-23 |
| NO744534L (enrdf_load_stackoverflow) | 1975-07-21 |
| DE2458625B2 (de) | 1980-07-10 |
| FI365774A7 (enrdf_load_stackoverflow) | 1975-06-22 |
| NO149735C (no) | 1984-06-13 |
| DE2458625A1 (de) | 1975-07-03 |
| DK138985B (da) | 1978-11-27 |
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