DE1695380C3 - 3-Hydrazinopyridazinderivate und Verfahren zu ihrer Herstellung - Google Patents
3-Hydrazinopyridazinderivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1695380C3 DE1695380C3 DE19681695380 DE1695380A DE1695380C3 DE 1695380 C3 DE1695380 C3 DE 1695380C3 DE 19681695380 DE19681695380 DE 19681695380 DE 1695380 A DE1695380 A DE 1695380A DE 1695380 C3 DE1695380 C3 DE 1695380C3
- Authority
- DE
- Germany
- Prior art keywords
- hydrazino
- processes
- preparation
- morpholinopyridazine
- blood pressure
- 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
- YTRGNBTVTHPFJM-UHFFFAOYSA-N pyridazin-3-ylhydrazine Chemical class NNC1=CC=CN=N1 YTRGNBTVTHPFJM-UHFFFAOYSA-N 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 4
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000036772 blood pressure Effects 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 229960002474 hydralazine Drugs 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- -1 4-methylpiperazino form Chemical group 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PHBNMZNMGUQCFK-UHFFFAOYSA-N (6-morpholin-4-ylpyridazin-3-yl)hydrazine Chemical compound N1=NC(NN)=CC=C1N1CCOCC1 PHBNMZNMGUQCFK-UHFFFAOYSA-N 0.000 description 2
- WLDKNDQFNZDHEA-UHFFFAOYSA-N 4-pyridazin-3-ylmorpholine Chemical compound C1COCCN1C1=CC=CN=N1 WLDKNDQFNZDHEA-UHFFFAOYSA-N 0.000 description 2
- PHGLUIAXQDYMBW-UHFFFAOYSA-N 6-morpholin-4-yl-N-(propan-2-ylideneamino)pyridazin-3-amine Chemical compound C(C)(C)=NNC=1N=NC(=CC1)N1CCOCC1 PHGLUIAXQDYMBW-UHFFFAOYSA-N 0.000 description 2
- CNFVMFCQXDOWAM-UHFFFAOYSA-N CN1CCN(CC1)C1=CC=C(NN=C(C)C)N=N1 Chemical compound CN1CCN(CC1)C1=CC=C(NN=C(C)C)N=N1 CNFVMFCQXDOWAM-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FPAOMVHSUQKCIG-UHFFFAOYSA-N [6-(4-methylpiperazin-1-yl)pyridazin-3-yl]hydrazine Chemical compound C1CN(C)CCN1C1=CC=C(NN)N=N1 FPAOMVHSUQKCIG-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OJYGBLRPYBAHRT-IPQSZEQASA-N chloralose Chemical compound O1[C@H](C(Cl)(Cl)Cl)O[C@@H]2[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]21 OJYGBLRPYBAHRT-IPQSZEQASA-N 0.000 description 1
- 229950009941 chloralose Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000035488 systolic blood pressure 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D237/20—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3804/67A GB1168334A (en) | 1967-01-25 | 1967-01-25 | New Pharmacologically Active Pyridazines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1695380A1 DE1695380A1 (de) | 1972-08-10 |
| DE1695380B2 DE1695380B2 (de) | 1973-11-08 |
| DE1695380C3 true DE1695380C3 (de) | 1974-07-04 |
Family
ID=9765208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681695380 Expired DE1695380C3 (de) | 1967-01-25 | 1968-01-12 | 3-Hydrazinopyridazinderivate und Verfahren zu ihrer Herstellung |
Country Status (15)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1298210A (en) * | 1968-12-30 | 1972-11-29 | Sandoz Ltd | Improvements in or relating to dihalo-pyridazine derivatives |
| IT1054107B (it) * | 1970-12-15 | 1981-11-10 | Isf Spa | Nuove 3,idrazinopiridazine 6,sostituite ad attivita antiiperten siva e loro preparazione |
| DE2965377D1 (en) * | 1978-10-02 | 1983-06-16 | Lepetit Spa | 6-amino substituted n-pyrrolyl-3-pyridazine amines, their preparation, and pharmaceutically antihypertensive compositions containing them |
-
1967
- 1967-01-25 GB GB3804/67A patent/GB1168334A/en not_active Expired
- 1967-12-29 IL IL2924867A patent/IL29248A/xx unknown
-
1968
- 1968-01-11 NL NL6800466A patent/NL6800466A/xx unknown
- 1968-01-12 DE DE19681695380 patent/DE1695380C3/de not_active Expired
- 1968-01-16 SE SE54168A patent/SE337382B/xx unknown
- 1968-01-22 FI FI16668A patent/FI47663C/fi active
- 1968-01-22 FR FR1568058D patent/FR1568058A/fr not_active Expired
- 1968-01-23 CH CH101668A patent/CH471132A/fr not_active IP Right Cessation
- 1968-01-24 NO NO30368A patent/NO120683B/no unknown
- 1968-01-24 AT AT70768A patent/AT271491B/de active
- 1968-01-24 DK DK26468A patent/DK117301B/da not_active IP Right Cessation
- 1968-01-24 BR BR19648568A patent/BR6896485D0/pt unknown
- 1968-01-25 YU YU18468A patent/YU32078B/xx unknown
- 1968-01-25 BE BE709868D patent/BE709868A/xx not_active IP Right Cessation
- 1968-01-25 ES ES349741A patent/ES349741A1/es not_active Expired
- 1968-03-29 FR FR146475A patent/FR7580M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1695380A1 (de) | 1972-08-10 |
| NO120683B (enrdf_load_stackoverflow) | 1970-11-23 |
| BR6896485D0 (pt) | 1973-05-10 |
| NL6800466A (enrdf_load_stackoverflow) | 1968-07-26 |
| AT271491B (de) | 1969-06-10 |
| BE709868A (enrdf_load_stackoverflow) | 1968-05-30 |
| DK117301B (da) | 1970-04-13 |
| YU32078B (en) | 1974-04-30 |
| CH471132A (fr) | 1969-04-15 |
| FI47663C (fi) | 1974-02-11 |
| FR1568058A (enrdf_load_stackoverflow) | 1969-05-23 |
| YU18468A (en) | 1973-10-31 |
| GB1168334A (en) | 1969-10-22 |
| FR7580M (enrdf_load_stackoverflow) | 1970-01-05 |
| IL29248A (en) | 1971-10-20 |
| DE1695380B2 (de) | 1973-11-08 |
| FI47663B (enrdf_load_stackoverflow) | 1973-10-31 |
| ES349741A1 (es) | 1969-04-01 |
| SE337382B (enrdf_load_stackoverflow) | 1971-08-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2235544C3 (de) | 33-Disubstituierte l-Methyl-1,2,4triazolderivate und Verfahren zu deren Herstellung | |
| DE19926233C1 (de) | Verfahren zur Herstellung von Thiazolidin | |
| DE2228363A1 (de) | 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE1493579B1 (de) | Verfahren zur Herstellung neuer pharmazeutisch wertvoller Verbindungen | |
| DE2009743A1 (de) | Substituierte Biguanide mit antihyperglykämischer Wirkung | |
| DE2238504B2 (de) | l-Phenoxy-3-alkylaminopropan-2-ol -Derivate | |
| DE1445186B2 (de) | 3,3'-Di-2-imidazolin-2-yl-carbanilid | |
| DE1695380C3 (de) | 3-Hydrazinopyridazinderivate und Verfahren zu ihrer Herstellung | |
| DE1949813B2 (de) | 3-(4-PyrWyl)-4-(2-hydroxyphenyl)-5-alkyl-pyrazole | |
| DE2921660A1 (de) | 5-nitroimidazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende antiprotozoen-mittel | |
| DE3326148C2 (enrdf_load_stackoverflow) | ||
| DE1545772B1 (de) | 7-(3'-Picolylamino-alkyl)-theophylline und deren nikotinsaure Salze | |
| DE2221758A1 (de) | Yohimbinderivate,Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1965711C3 (de) | l^-Dihydro-133-triazin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE1925351A1 (de) | 3-Isopropylnorbornanamine und Verfahren zu ihrer Herstellung | |
| DE2923817C2 (de) | (3-Alkylamino-2-hydroxyproposy)-furan-2-carbonsäureanilide und deren physiologisch verträgliche Säureadditionssalze und Verfahren zu deren Herstellung sowie Arzneimittel mit einem Gehalt dieser Verbindungen | |
| DE3438244C2 (enrdf_load_stackoverflow) | ||
| DE2336670A1 (de) | Aminoaether von o-thymotinsaeureestern | |
| DE2536170C3 (de) | Flavonderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2023829C3 (de) | Kernsubstituierte 3-Phenoxy-lphenoxyalkyl-amino-propan-2-oIe, Verfahren zu ihrer Herstellung sowie Arzneimittel | |
| DE2310827C3 (de) | Im phenylkern heterocyclisch substituierte Phenylalaninderivate | |
| DE2725245A1 (de) | Methylaminderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische oder veterinaermedizinische zusammensetzungen | |
| EP0185988B1 (de) | 10,11-Dihydro-5H-dibenzo[a,d]cycloheptadien-Derivate, ihre Herstellung und Verwendung | |
| DE2164618A1 (de) | Verbindung mit antihypertensiver Wir kung und Verfahren zu ihrer Herstellung | |
| DE2440378A1 (de) | Arzneimittel mit antiphlogistischen und analgetischen eigenschaften |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |