GB1086953A - Method for the total synthesis of a category of chemical derivatives having a papaverolinic structure - Google Patents
Method for the total synthesis of a category of chemical derivatives having a papaverolinic structureInfo
- Publication number
- GB1086953A GB1086953A GB3908664A GB3908664A GB1086953A GB 1086953 A GB1086953 A GB 1086953A GB 3908664 A GB3908664 A GB 3908664A GB 3908664 A GB3908664 A GB 3908664A GB 1086953 A GB1086953 A GB 1086953A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- dibenzoyloxy
- resulting
- papaveroline
- amide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title 1
- 238000006257 total synthesis reaction Methods 0.000 title 1
- 229950005542 papaveroline Drugs 0.000 abstract 5
- 150000001408 amides Chemical class 0.000 abstract 4
- MXQKCNCLQIHHJA-UHFFFAOYSA-N papaveroline Chemical class C1=C(O)C(O)=CC=C1CC1=NC=CC2=CC(O)=C(O)C=C12 MXQKCNCLQIHHJA-UHFFFAOYSA-N 0.000 abstract 4
- 150000001412 amines Chemical class 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- HOJDBBOGGNWLPJ-UHFFFAOYSA-N [2-benzoyloxy-4-(2-chloro-2-oxoethyl)phenyl] benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1=C(C=C(C=C1)CC(=O)Cl)OC(C1=CC=CC=C1)=O HOJDBBOGGNWLPJ-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- -1 chloroformylmethyl compound Chemical class 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- KARYFJLZXGWDIM-UHFFFAOYSA-N (2-benzoyloxy-4-methylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC(C)=CC=C1OC(=O)C1=CC=CC=C1 KARYFJLZXGWDIM-UHFFFAOYSA-N 0.000 abstract 1
- LVTPRIAGCBEGPW-UHFFFAOYSA-N (2-benzoyloxyphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1OC(=O)C1=CC=CC=C1 LVTPRIAGCBEGPW-UHFFFAOYSA-N 0.000 abstract 1
- OPYJIAODVQQOOJ-UHFFFAOYSA-N (6-benzoyloxy-6-formylcyclohexa-2,4-dien-1-yl) benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1(C=O)C(C=CC=C1)OC(C1=CC=CC=C1)=O OPYJIAODVQQOOJ-UHFFFAOYSA-N 0.000 abstract 1
- GIRVSIBBHKMUQQ-UHFFFAOYSA-N 2-(3,4-dibenzoyloxyphenyl)-2-hydroxyacetic acid Chemical compound C(C1=CC=CC=C1)(=O)OC1=C(C=C(C=C1)C(C(=O)O)O)OC(C1=CC=CC=C1)=O GIRVSIBBHKMUQQ-UHFFFAOYSA-N 0.000 abstract 1
- UCWSTFWSEJHACS-UHFFFAOYSA-N 2-(3,4-dibenzoyloxyphenyl)acetic acid Chemical compound C=1C=CC=CC=1C(=O)OC1=CC(CC(=O)O)=CC=C1OC(=O)C1=CC=CC=C1 UCWSTFWSEJHACS-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 abstract 1
- 150000002832 nitroso derivatives Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- 239000012286 potassium permanganate Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229910001023 sodium amalgam Inorganic materials 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1294464 | 1964-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1086953A true GB1086953A (en) | 1967-10-11 |
Family
ID=11143880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3908664A Expired GB1086953A (en) | 1964-06-15 | 1964-09-25 | Method for the total synthesis of a category of chemical derivatives having a papaverolinic structure |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE656788A (enrdf_load_stackoverflow) |
| BR (1) | BR6572326D0 (enrdf_load_stackoverflow) |
| CH (1) | CH467261A (enrdf_load_stackoverflow) |
| FR (1) | FR5545M (enrdf_load_stackoverflow) |
| GB (1) | GB1086953A (enrdf_load_stackoverflow) |
-
1964
- 1964-09-25 GB GB3908664A patent/GB1086953A/en not_active Expired
- 1964-12-08 BE BE656788A patent/BE656788A/xx unknown
- 1964-12-30 CH CH1682364A patent/CH467261A/fr unknown
-
1965
- 1965-06-14 FR FR20708A patent/FR5545M/fr not_active Expired
- 1965-06-15 BR BR17232665A patent/BR6572326D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE656788A (enrdf_load_stackoverflow) | 1965-04-01 |
| FR5545M (enrdf_load_stackoverflow) | 1967-12-26 |
| CH467261A (fr) | 1969-01-15 |
| BR6572326D0 (pt) | 1973-10-25 |
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