NO810126L - Fremgangsmaate for fremstilling av nye pyridazinderivater - Google Patents
Fremgangsmaate for fremstilling av nye pyridazinderivaterInfo
- Publication number
- NO810126L NO810126L NO810126A NO810126A NO810126L NO 810126 L NO810126 L NO 810126L NO 810126 A NO810126 A NO 810126A NO 810126 A NO810126 A NO 810126A NO 810126 L NO810126 L NO 810126L
- Authority
- NO
- Norway
- Prior art keywords
- alkylaminophenyl
- phenyl
- aminophenyl
- hydrogen atom
- acetamidophenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical class C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 title description 5
- -1 halogenophenyl Chemical group 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract description 6
- 125000006501 nitrophenyl group Chemical group 0.000 claims abstract description 6
- 125000002541 furyl group Chemical group 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 150000007513 acids Chemical class 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- NMMRZZDSXSOKRU-UHFFFAOYSA-N 2,3-dihydroimidazo[1,2-b]pyridazine Chemical class N1=CC=CC2=NCCN21 NMMRZZDSXSOKRU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 201000003004 ptosis Diseases 0.000 description 2
- 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 2
- 229960003147 reserpine Drugs 0.000 description 2
- 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 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8000926A FR2473522A1 (fr) | 1980-01-16 | 1980-01-16 | Nouveaux derives substitues de dihydro-2,3 imidazo(1,2-b)pyridazines et les medicaments, utiles notamment comme antidepresseurs, qui en contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO810126L true NO810126L (no) | 1981-07-17 |
Family
ID=9237594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO810126A NO810126L (no) | 1980-01-16 | 1981-01-15 | Fremgangsmaate for fremstilling av nye pyridazinderivater |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4353903A (de) |
| EP (1) | EP0032856B1 (de) |
| JP (1) | JPS56103183A (de) |
| AT (1) | ATE2431T1 (de) |
| AU (1) | AU538882B2 (de) |
| CA (1) | CA1155118A (de) |
| DE (1) | DE3160044D1 (de) |
| DK (1) | DK17581A (de) |
| ES (1) | ES498541A0 (de) |
| FI (1) | FI810103L (de) |
| FR (1) | FR2473522A1 (de) |
| GR (1) | GR73647B (de) |
| IL (1) | IL61911A (de) |
| NO (1) | NO810126L (de) |
| NZ (1) | NZ196018A (de) |
| PT (1) | PT72359B (de) |
| ZA (1) | ZA81269B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2511366A1 (fr) * | 1981-08-11 | 1983-02-18 | Sanofi Sa | Nouveaux derives de la pyridazine, leur procede de preparation et les medicaments, actifs sur le systeme nerveux central, qui en contiennent |
| GB8334210D0 (en) * | 1983-12-22 | 1984-02-01 | Roussel Lab Ltd | Imidazo(1 2-c)pyrimidines |
| US4569934A (en) * | 1984-10-09 | 1986-02-11 | American Cyanamid Company | Imidazo[1,2-b]pyridazines |
| FR2619818B1 (fr) * | 1987-09-01 | 1990-01-12 | Sanofi Sa | Imidazo (1,2-b) pyridazines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| PH27291A (en) * | 1989-01-31 | 1993-05-04 | Takeda Chemical Industries Ltd | Imidazolpyrimidazines their production and use |
| WO2021193897A1 (ja) * | 2020-03-27 | 2021-09-30 | アステラス製薬株式会社 | 置換ピリダジン化合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3828041A (en) * | 1971-02-24 | 1974-08-06 | American Cyanamid Co | 6-substituted 3-nitroimidazo(1,2-b)pyridazines and method of preparing same |
| CA1080712A (en) * | 1976-09-22 | 1980-07-01 | Jay D. Albright | Hypotensive agents |
| GB1583911A (en) * | 1977-02-09 | 1981-02-04 | Allen & Hanburys Ltd | Imidazopyridazines and their use as therapeutic agents |
-
1980
- 1980-01-16 FR FR8000926A patent/FR2473522A1/fr active Granted
-
1981
- 1981-01-07 GR GR63871A patent/GR73647B/el unknown
- 1981-01-13 DE DE8181400036T patent/DE3160044D1/de not_active Expired
- 1981-01-13 EP EP81400036A patent/EP0032856B1/de not_active Expired
- 1981-01-13 AT AT81400036T patent/ATE2431T1/de not_active IP Right Cessation
- 1981-01-15 ES ES498541A patent/ES498541A0/es active Granted
- 1981-01-15 ZA ZA00810269A patent/ZA81269B/xx unknown
- 1981-01-15 PT PT72359A patent/PT72359B/pt unknown
- 1981-01-15 FI FI810103A patent/FI810103L/fi not_active Application Discontinuation
- 1981-01-15 DK DK17581A patent/DK17581A/da unknown
- 1981-01-15 AU AU66242/81A patent/AU538882B2/en not_active Ceased
- 1981-01-15 NO NO810126A patent/NO810126L/no unknown
- 1981-01-15 NZ NZ196018A patent/NZ196018A/xx unknown
- 1981-01-15 US US06/225,265 patent/US4353903A/en not_active Expired - Fee Related
- 1981-01-15 CA CA000368548A patent/CA1155118A/en not_active Expired
- 1981-01-15 IL IL61911A patent/IL61911A/xx unknown
- 1981-01-16 JP JP582481A patent/JPS56103183A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI810103L (fi) | 1981-07-17 |
| PT72359B (fr) | 1981-12-18 |
| ES8203896A1 (es) | 1982-04-16 |
| ZA81269B (en) | 1982-02-24 |
| NZ196018A (en) | 1982-09-14 |
| ATE2431T1 (de) | 1983-03-15 |
| DK17581A (da) | 1981-07-17 |
| IL61911A (en) | 1983-10-31 |
| DE3160044D1 (en) | 1983-03-17 |
| EP0032856B1 (de) | 1983-02-09 |
| FR2473522A1 (fr) | 1981-07-17 |
| JPS56103183A (en) | 1981-08-18 |
| IL61911A0 (en) | 1981-02-27 |
| AU538882B2 (en) | 1984-08-30 |
| FR2473522B1 (de) | 1982-09-17 |
| ES498541A0 (es) | 1982-04-16 |
| EP0032856A1 (de) | 1981-07-29 |
| GR73647B (de) | 1984-03-26 |
| US4353903A (en) | 1982-10-12 |
| CA1155118A (en) | 1983-10-11 |
| AU6624281A (en) | 1981-07-23 |
| PT72359A (fr) | 1981-02-01 |
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