DE2309367A1 - 1,4-dihydro-4-h-isochinolinderivate und verfahren zu ihrer herstellung - Google Patents
1,4-dihydro-4-h-isochinolinderivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2309367A1 DE2309367A1 DE19732309367 DE2309367A DE2309367A1 DE 2309367 A1 DE2309367 A1 DE 2309367A1 DE 19732309367 DE19732309367 DE 19732309367 DE 2309367 A DE2309367 A DE 2309367A DE 2309367 A1 DE2309367 A1 DE 2309367A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- dihydro
- hoe
- hydrogen
- 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.)
- Pending
Links
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- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical class C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229960001989 prenylamine Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- 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
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732309367 DE2309367A1 (de) | 1973-02-24 | 1973-02-24 | 1,4-dihydro-4-h-isochinolinderivate und verfahren zu ihrer herstellung |
| IL44208A IL44208A0 (en) | 1973-02-24 | 1974-02-14 | 1,4-dihydro-2-h-isoquinoline derivatives and process for their manufacture |
| CA192,842A CA1016173A (en) | 1973-02-24 | 1974-02-18 | 1,4-dihydro-2-h-isoquinoline derivatives and process for their manufacture |
| NL7402259A NL7402259A (enExample) | 1973-02-24 | 1974-02-19 | |
| DD176704A DD114408A5 (enExample) | 1973-02-24 | 1974-02-20 | |
| GB817174A GB1457186A (en) | 1973-02-24 | 1974-02-22 | Isoquinoline derivatives and process for their manufacture |
| AT146874A ATA146874A (de) | 1973-02-24 | 1974-02-22 | Verfahren zur herstellung von neuen 1,4-dihydro-2h-isochinolinderivaten |
| IE00358/74A IE38917B1 (en) | 1973-02-24 | 1974-02-22 | Isoquinoline derivatives and process for their manufactur |
| FR7406209A FR2218892B1 (enExample) | 1973-02-24 | 1974-02-22 | |
| ZA00741172A ZA741172B (en) | 1973-02-24 | 1974-02-22 | 1,4-dihydro-2-h-isoquinoline derivatives and process for their manufacture |
| JP49021064A JPS49117475A (enExample) | 1973-02-24 | 1974-02-23 | |
| AU65930/74A AU6593074A (en) | 1973-02-24 | 1974-02-25 | 1, 4-dihydro-2-h-isoquinoline |
| BE141348A BE811528A (fr) | 1973-02-24 | 1974-02-25 | Derives de la 1 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732309367 DE2309367A1 (de) | 1973-02-24 | 1973-02-24 | 1,4-dihydro-4-h-isochinolinderivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2309367A1 true DE2309367A1 (de) | 1974-09-05 |
Family
ID=5873034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732309367 Pending DE2309367A1 (de) | 1973-02-24 | 1973-02-24 | 1,4-dihydro-4-h-isochinolinderivate und verfahren zu ihrer herstellung |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS49117475A (enExample) |
| AT (1) | ATA146874A (enExample) |
| AU (1) | AU6593074A (enExample) |
| BE (1) | BE811528A (enExample) |
| CA (1) | CA1016173A (enExample) |
| DD (1) | DD114408A5 (enExample) |
| DE (1) | DE2309367A1 (enExample) |
| FR (1) | FR2218892B1 (enExample) |
| GB (1) | GB1457186A (enExample) |
| IE (1) | IE38917B1 (enExample) |
| IL (1) | IL44208A0 (enExample) |
| NL (1) | NL7402259A (enExample) |
| ZA (1) | ZA741172B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8328052D0 (en) * | 1983-10-20 | 1983-11-23 | Beecham Group Plc | Compounds |
| CN111039867A (zh) * | 2019-12-11 | 2020-04-21 | 四川大学 | 一种室温光照促进的3,4-二取代异喹啉衍生物绿色合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1354246A (en) * | 1971-05-27 | 1974-06-05 | Egyt Gyogyszervegyeszeti Gyar | 1,4-dihydro-3-2h-isoquinoline derivatives and a process for the preparation thereof |
-
1973
- 1973-02-24 DE DE19732309367 patent/DE2309367A1/de active Pending
-
1974
- 1974-02-14 IL IL44208A patent/IL44208A0/xx unknown
- 1974-02-18 CA CA192,842A patent/CA1016173A/en not_active Expired
- 1974-02-19 NL NL7402259A patent/NL7402259A/xx unknown
- 1974-02-20 DD DD176704A patent/DD114408A5/xx unknown
- 1974-02-22 ZA ZA00741172A patent/ZA741172B/xx unknown
- 1974-02-22 FR FR7406209A patent/FR2218892B1/fr not_active Expired
- 1974-02-22 GB GB817174A patent/GB1457186A/en not_active Expired
- 1974-02-22 AT AT146874A patent/ATA146874A/de not_active Application Discontinuation
- 1974-02-22 IE IE00358/74A patent/IE38917B1/xx unknown
- 1974-02-23 JP JP49021064A patent/JPS49117475A/ja active Pending
- 1974-02-25 BE BE141348A patent/BE811528A/xx unknown
- 1974-02-25 AU AU65930/74A patent/AU6593074A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL44208A0 (en) | 1974-05-16 |
| FR2218892A1 (enExample) | 1974-09-20 |
| GB1457186A (en) | 1976-12-01 |
| DD114408A5 (enExample) | 1975-08-05 |
| ATA146874A (de) | 1977-08-15 |
| AU6593074A (en) | 1975-08-28 |
| FR2218892B1 (enExample) | 1978-01-06 |
| NL7402259A (enExample) | 1974-08-27 |
| IE38917L (en) | 1974-08-24 |
| ZA741172B (en) | 1975-01-29 |
| IE38917B1 (en) | 1978-06-21 |
| JPS49117475A (enExample) | 1974-11-09 |
| BE811528A (fr) | 1974-08-26 |
| CA1016173A (en) | 1977-08-23 |
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