FI66380C - Foerfarande foer framstaellning av nya antireproduktiva 1,2,4-triazolo(5,1-a)isoindoler -isokinoliner och -bensazepiner - Google Patents
Foerfarande foer framstaellning av nya antireproduktiva 1,2,4-triazolo(5,1-a)isoindoler -isokinoliner och -bensazepiner Download PDFInfo
- Publication number
- FI66380C FI66380C FI793215A FI793215A FI66380C FI 66380 C FI66380 C FI 66380C FI 793215 A FI793215 A FI 793215A FI 793215 A FI793215 A FI 793215A FI 66380 C FI66380 C FI 66380C
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- FI
- Finland
- Prior art keywords
- compounds
- triazolo
- compound
- formula
- antireproductive
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007269 dehydrobromination reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002518 isoindoles Chemical class 0.000 description 1
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229930185711 monocolin Natural products 0.000 description 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7842415 | 1978-10-30 | ||
| GB7842415 | 1978-10-30 | ||
| US06/087,371 US4275066A (en) | 1978-10-30 | 1979-10-23 | Antireproductive tricyclic ortho-fused nitrogen containing compounds |
| US8737179 | 1979-10-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI793215A7 FI793215A7 (fi) | 1980-05-01 |
| FI66380B FI66380B (fi) | 1984-06-29 |
| FI66380C true FI66380C (fi) | 1984-10-10 |
Family
ID=26269380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI793215A FI66380C (fi) | 1978-10-30 | 1979-10-16 | Foerfarande foer framstaellning av nya antireproduktiva 1,2,4-triazolo(5,1-a)isoindoler -isokinoliner och -bensazepiner |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4275066A (en, 2012) |
| JP (1) | JPS5562086A (en, 2012) |
| AT (2) | AT374803B (en, 2012) |
| AU (1) | AU532045B2 (en, 2012) |
| BE (1) | BE879729A (en, 2012) |
| CA (1) | CA1123827A (en, 2012) |
| CH (1) | CH650261A5 (en, 2012) |
| DE (1) | DE2943286A1 (en, 2012) |
| DK (1) | DK154298C (en, 2012) |
| FI (1) | FI66380C (en, 2012) |
| FR (1) | FR2440370A1 (en, 2012) |
| GB (1) | GB2039888B (en, 2012) |
| GR (1) | GR70248B (en, 2012) |
| HK (1) | HK24383A (en, 2012) |
| IE (1) | IE49625B1 (en, 2012) |
| LU (1) | LU81833A1 (en, 2012) |
| NL (1) | NL7907783A (en, 2012) |
| ZA (1) | ZA795743B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1211437A (en) * | 1981-08-12 | 1986-09-16 | Rene Borer | Benzazepines |
| US5302589A (en) * | 1992-08-07 | 1994-04-12 | Glaxo, Inc. | Heterocyclic inhibitors of 5-α-testosterone reductase |
| CN100432074C (zh) * | 2006-06-29 | 2008-11-12 | 浙江大学 | 2-芳基咪唑并[2,1-a]异喹啉的合成方法 |
| JP5412809B2 (ja) * | 2008-11-21 | 2014-02-12 | コニカミノルタ株式会社 | イミダゾール化合物の製造方法 |
| RU2657832C1 (ru) * | 2017-06-07 | 2018-06-15 | федеральное государственное автономное образовательное учреждение высшего образования "Южный федеральный университет" | Антидиабетическое средство |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758480A (en) * | 1968-07-10 | 1973-09-11 | Mallinckrodt Chemical Works | S-triazolo(5,1-a)isoquinolines and derivatives thereof |
| US3775417A (en) * | 1971-08-05 | 1973-11-27 | Mallinckrodt Chemical Works | Selective hydrogenation of tri-and tetrazoloisoquinolines |
| RO66059A (ro) * | 1973-05-25 | 1981-05-30 | Gruppo Lepetit Spa,It | Procedeu de obtinere a unor derivati de triazolochinoline |
| GB1477302A (en) * | 1973-05-25 | 1977-06-22 | Lepetit Spa | Triazolo-isoindole and triazolo-isoquinoline derivatives and their manufacture and uses |
| US4075341A (en) * | 1974-05-24 | 1978-02-21 | Gruppo Lepetit S.P.A. | 2-Substituted phenyl-5-triazols [5,1-a] isoquinoline compounds |
| GB1484615A (en) * | 1974-11-23 | 1977-09-01 | Lepetit Spa | Tricyclic n-containing derivatives |
| IT1054655B (it) * | 1975-08-27 | 1981-11-30 | Lepetit Spa | Derivati condensati del l isochinolina |
| DE2707272C2 (de) * | 1977-02-19 | 1982-12-02 | Gruppo Lepetit S.p.A., 20158 Milano | 2-(p-Chlorphenyl)-s-triazolo [5,1-a] isochinolin |
| US4093728A (en) * | 1977-08-18 | 1978-06-06 | E. R. Squibb & Sons, Inc. | Triazoloisoindoles |
-
1979
- 1979-10-13 GR GR60257A patent/GR70248B/el unknown
- 1979-10-16 FI FI793215A patent/FI66380C/fi not_active IP Right Cessation
- 1979-10-18 AU AU51908/79A patent/AU532045B2/en not_active Ceased
- 1979-10-23 US US06/087,371 patent/US4275066A/en not_active Expired - Lifetime
- 1979-10-23 NL NL7907783A patent/NL7907783A/nl not_active Application Discontinuation
- 1979-10-26 ZA ZA00795743A patent/ZA795743B/xx unknown
- 1979-10-26 DE DE19792943286 patent/DE2943286A1/de active Granted
- 1979-10-26 IE IE2067/79A patent/IE49625B1/en unknown
- 1979-10-26 DK DK452779A patent/DK154298C/da not_active IP Right Cessation
- 1979-10-29 CH CH9672/79A patent/CH650261A5/it not_active IP Right Cessation
- 1979-10-29 GB GB7937388A patent/GB2039888B/en not_active Expired
- 1979-10-29 JP JP13971079A patent/JPS5562086A/ja active Granted
- 1979-10-29 LU LU81833A patent/LU81833A1/fr unknown
- 1979-10-29 AT AT0697179A patent/AT374803B/de not_active IP Right Cessation
- 1979-10-30 FR FR7926902A patent/FR2440370A1/fr active Granted
- 1979-10-30 CA CA338,698A patent/CA1123827A/en not_active Expired
- 1979-10-30 BE BE0/197894A patent/BE879729A/fr not_active IP Right Cessation
-
1983
- 1983-06-20 AT AT0226083A patent/AT384427B/de not_active IP Right Cessation
- 1983-07-28 HK HK243/83A patent/HK24383A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2943286A1 (de) | 1980-05-14 |
| LU81833A1 (fr) | 1980-05-07 |
| IE792067L (en) | 1980-04-30 |
| AU5190879A (en) | 1980-05-08 |
| HK24383A (en) | 1983-08-05 |
| DK452779A (da) | 1980-05-01 |
| DE2943286C2 (en, 2012) | 1990-05-23 |
| ATA226083A (de) | 1987-04-15 |
| JPS6354716B2 (en, 2012) | 1988-10-28 |
| FR2440370B1 (en, 2012) | 1982-10-29 |
| US4275066A (en) | 1981-06-23 |
| AT384427B (de) | 1987-11-10 |
| JPS5562086A (en) | 1980-05-10 |
| DK154298B (da) | 1988-10-31 |
| FI66380B (fi) | 1984-06-29 |
| ZA795743B (en) | 1980-10-29 |
| GB2039888B (en) | 1982-11-03 |
| IE49625B1 (en) | 1985-11-13 |
| AT374803B (de) | 1984-06-12 |
| BE879729A (fr) | 1980-04-30 |
| FI793215A7 (fi) | 1980-05-01 |
| GR70248B (en, 2012) | 1982-09-01 |
| CA1123827A (en) | 1982-05-18 |
| CH650261A5 (it) | 1985-07-15 |
| DK154298C (da) | 1989-03-28 |
| AU532045B2 (en) | 1983-09-15 |
| NL7907783A (nl) | 1980-05-02 |
| ATA697179A (de) | 1983-10-15 |
| GB2039888A (en) | 1980-08-20 |
| FR2440370A1 (fr) | 1980-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: GRUPPO LEPETIT S.P.A. |