CH617688A5 - Process for the preparation of new acetamidoxime derivatives - Google Patents
Process for the preparation of new acetamidoxime derivatives Download PDFInfo
- Publication number
- CH617688A5 CH617688A5 CH1603476A CH1603476A CH617688A5 CH 617688 A5 CH617688 A5 CH 617688A5 CH 1603476 A CH1603476 A CH 1603476A CH 1603476 A CH1603476 A CH 1603476A CH 617688 A5 CH617688 A5 CH 617688A5
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl
- benzofuranyl
- methyl
- acetamidoxime
- morpholino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 39
- 238000002360 preparation method Methods 0.000 title claims description 28
- AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical class CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 title claims description 18
- 230000008569 process Effects 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- 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 abstract 2
- -1 dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, pyrrolidino, morpholino, piperidino, heptamethyleneimino group Chemical group 0.000 claims description 132
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000004872 arterial blood pressure Effects 0.000 abstract description 2
- 230000001575 pathological effect Effects 0.000 abstract description 2
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 230000002269 spontaneous effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 108
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 38
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000002220 antihypertensive agent Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
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- 238000010992 reflux Methods 0.000 description 5
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
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- 230000036325 urinary excretion Effects 0.000 description 4
- RWCHGCSLPRNFRX-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)acetonitrile Chemical compound C1=CC=C2C(CC#N)=C(CC)OC2=C1 RWCHGCSLPRNFRX-UHFFFAOYSA-N 0.000 description 3
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 3
- 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 3
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- 210000004100 adrenal gland Anatomy 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- NOCUHXPGWAPFGO-UHFFFAOYSA-N butan-2-one;propan-2-ol Chemical compound CC(C)O.CCC(C)=O NOCUHXPGWAPFGO-UHFFFAOYSA-N 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
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- 231100001231 less toxic Toxicity 0.000 description 1
- 201000005857 malignant hypertension Diseases 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- OPENCMFJZQABIY-UHFFFAOYSA-N n'-hydroxybutanimidamide Chemical compound CCCC(N)=NO OPENCMFJZQABIY-UHFFFAOYSA-N 0.000 description 1
- RLZPCFQNZGINRP-UHFFFAOYSA-N n'-hydroxypropanimidamide Chemical compound CCC(N)=NO RLZPCFQNZGINRP-UHFFFAOYSA-N 0.000 description 1
- 210000004126 nerve fiber Anatomy 0.000 description 1
- 210000000826 nictitating membrane Anatomy 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- ZDYUUBIMAGBMPY-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O ZDYUUBIMAGBMPY-UHFFFAOYSA-N 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 229950000494 pentamethonium bromide Drugs 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- HHAVHBDPWSUKHZ-UHFFFAOYSA-N propan-2-ol;propan-2-one Chemical compound CC(C)O.CC(C)=O HHAVHBDPWSUKHZ-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000000194 sympathicotonic effect Effects 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940057613 veratrum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB52475/75A GB1508210A (en) | 1975-12-22 | 1975-12-22 | Benzofuran-derived amidoximes and process for preparing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617688A5 true CH617688A5 (en) | 1980-06-13 |
Family
ID=10464059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1603476A CH617688A5 (en) | 1975-12-22 | 1976-12-20 | Process for the preparation of new acetamidoxime derivatives |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS52102268A (OSRAM) |
| AR (1) | AR212605A1 (OSRAM) |
| AT (1) | AT354430B (OSRAM) |
| AU (1) | AU503931B2 (OSRAM) |
| BE (1) | BE849430A (OSRAM) |
| CA (1) | CA1080723A (OSRAM) |
| CH (1) | CH617688A5 (OSRAM) |
| DD (1) | DD127762A5 (OSRAM) |
| DE (1) | DE2657902A1 (OSRAM) |
| DK (1) | DK577276A (OSRAM) |
| ES (1) | ES454421A1 (OSRAM) |
| FI (1) | FI60395C (OSRAM) |
| FR (1) | FR2336127A1 (OSRAM) |
| GB (1) | GB1508210A (OSRAM) |
| HU (1) | HU176557B (OSRAM) |
| IE (1) | IE44753B1 (OSRAM) |
| IT (1) | IT1123948B (OSRAM) |
| MX (1) | MX3927E (OSRAM) |
| NL (1) | NL7613753A (OSRAM) |
| NO (1) | NO144794C (OSRAM) |
| NZ (1) | NZ182809A (OSRAM) |
| OA (1) | OA05521A (OSRAM) |
| PL (1) | PL102695B1 (OSRAM) |
| PT (1) | PT65971B (OSRAM) |
| SE (1) | SE429233B (OSRAM) |
| SU (1) | SU598564A3 (OSRAM) |
| YU (1) | YU309376A (OSRAM) |
| ZA (1) | ZA767241B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3398941A1 (en) * | 2017-05-03 | 2018-11-07 | AXXAM S.p.A. | Heterocyclic p2x7 antagonists |
-
1975
- 1975-12-22 GB GB52475/75A patent/GB1508210A/en not_active Expired
-
1976
- 1976-12-03 IE IE2663/76A patent/IE44753B1/en unknown
- 1976-12-06 ZA ZA767241A patent/ZA767241B/xx unknown
- 1976-12-06 NZ NZ182809A patent/NZ182809A/xx unknown
- 1976-12-10 NL NL7613753A patent/NL7613753A/xx not_active Application Discontinuation
- 1976-12-13 AR AR265814A patent/AR212605A1/es active
- 1976-12-14 AU AU20534/76A patent/AU503931B2/en not_active Expired
- 1976-12-14 FR FR7637622A patent/FR2336127A1/fr active Granted
- 1976-12-15 BE BE173280A patent/BE849430A/xx not_active IP Right Cessation
- 1976-12-15 MX MX765235U patent/MX3927E/es unknown
- 1976-12-15 CA CA267,918A patent/CA1080723A/en not_active Expired
- 1976-12-15 FI FI763604A patent/FI60395C/fi not_active IP Right Cessation
- 1976-12-15 PT PT65971A patent/PT65971B/pt unknown
- 1976-12-20 CH CH1603476A patent/CH617688A5/fr not_active IP Right Cessation
- 1976-12-20 ES ES454421A patent/ES454421A1/es not_active Expired
- 1976-12-20 YU YU03093/76A patent/YU309376A/xx unknown
- 1976-12-21 DK DK577276A patent/DK577276A/da not_active Application Discontinuation
- 1976-12-21 AT AT948476A patent/AT354430B/de not_active IP Right Cessation
- 1976-12-21 HU HU76LA901A patent/HU176557B/hu unknown
- 1976-12-21 SU SU762430683A patent/SU598564A3/ru active
- 1976-12-21 PL PL1976194589A patent/PL102695B1/pl unknown
- 1976-12-21 NO NO76764332A patent/NO144794C/no unknown
- 1976-12-21 DE DE19762657902 patent/DE2657902A1/de not_active Withdrawn
- 1976-12-21 IT IT7630679A patent/IT1123948B/it active
- 1976-12-21 SE SE7614368A patent/SE429233B/xx unknown
- 1976-12-22 JP JP15558976A patent/JPS52102268A/ja active Pending
- 1976-12-22 DD DD7600196548A patent/DD127762A5/xx unknown
- 1976-12-22 OA OA56023A patent/OA05521A/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: SANOFI |
|
| PUE | Assignment |
Owner name: OMNIUM FINANCIER AQUITAINE POUR L'HYGIENE ET LA SA |
|
| PL | Patent ceased | ||
| PL | Patent ceased |