NO120683B - - Google Patents
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- Publication number
- NO120683B NO120683B NO30368A NO30368A NO120683B NO 120683 B NO120683 B NO 120683B NO 30368 A NO30368 A NO 30368A NO 30368 A NO30368 A NO 30368A NO 120683 B NO120683 B NO 120683B
- Authority
- NO
- Norway
- Prior art keywords
- pyridazine
- hydrazino
- morpholino
- lower alkyl
- preparation
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- -1 carboxy, phenyl Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- PHBNMZNMGUQCFK-UHFFFAOYSA-N (6-morpholin-4-ylpyridazin-3-yl)hydrazine Chemical compound N1=NC(NN)=CC=C1N1CCOCC1 PHBNMZNMGUQCFK-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 150000004892 pyridazines Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 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 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- ZUTZIMYUEFESGE-UHFFFAOYSA-N (6-piperidin-1-ylpyridazin-3-yl)hydrazine Chemical compound N1=NC(NN)=CC=C1N1CCCCC1 ZUTZIMYUEFESGE-UHFFFAOYSA-N 0.000 description 4
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CUGVKCJTONTOPS-UHFFFAOYSA-N (6-morpholin-4-ylpyridazin-3-yl)hydrazine;dihydrochloride Chemical compound Cl.Cl.N1=NC(NN)=CC=C1N1CCOCC1 CUGVKCJTONTOPS-UHFFFAOYSA-N 0.000 description 2
- GOCQGHHDQKPGGC-UHFFFAOYSA-N 3-piperidin-1-ylpyridazine Chemical compound C1CCCCN1C1=CC=CN=N1 GOCQGHHDQKPGGC-UHFFFAOYSA-N 0.000 description 2
- CHTSWZNXEKOLPM-UHFFFAOYSA-N 5-nitrothiophene-2-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)S1 CHTSWZNXEKOLPM-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229960002474 hydralazine Drugs 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940107700 pyruvic acid Drugs 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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 1
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 1
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 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
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 206010038464 renal hypertension Diseases 0.000 description 1
- 239000002904 solvent Substances 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
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 (1)
| Publication Number | Publication Date |
|---|---|
| NO120683B true NO120683B (ja) | 1970-11-23 |
Family
ID=9765208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO30368A NO120683B (ja) | 1967-01-25 | 1968-01-24 |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT271491B (ja) |
| BE (1) | BE709868A (ja) |
| BR (1) | BR6896485D0 (ja) |
| CH (1) | CH471132A (ja) |
| DE (1) | DE1695380C3 (ja) |
| DK (1) | DK117301B (ja) |
| ES (1) | ES349741A1 (ja) |
| FI (1) | FI47663C (ja) |
| FR (2) | FR1568058A (ja) |
| GB (1) | GB1168334A (ja) |
| IL (1) | IL29248A (ja) |
| NL (1) | NL6800466A (ja) |
| NO (1) | NO120683B (ja) |
| SE (1) | SE337382B (ja) |
| YU (1) | YU32078B (ja) |
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 |
| EP0009655B1 (en) * | 1978-10-02 | 1983-05-11 | Gruppo Lepetit S.P.A. | 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 FR FR1568058D patent/FR1568058A/fr not_active Expired
- 1968-01-22 FI FI16668A patent/FI47663C/fi active
- 1968-01-23 CH CH101668A patent/CH471132A/fr not_active IP Right Cessation
- 1968-01-24 DK DK26468A patent/DK117301B/da not_active IP Right Cessation
- 1968-01-24 NO NO30368A patent/NO120683B/no unknown
- 1968-01-24 BR BR19648568A patent/BR6896485D0/pt unknown
- 1968-01-24 AT AT70768A patent/AT271491B/de active
- 1968-01-25 YU YU18468A patent/YU32078B/xx unknown
- 1968-01-25 ES ES349741A patent/ES349741A1/es not_active Expired
- 1968-01-25 BE BE709868D patent/BE709868A/xx not_active IP Right Cessation
- 1968-03-29 FR FR146475A patent/FR7580M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR6896485D0 (pt) | 1973-05-10 |
| DE1695380C3 (de) | 1974-07-04 |
| DE1695380B2 (de) | 1973-11-08 |
| SE337382B (ja) | 1971-08-09 |
| NL6800466A (ja) | 1968-07-26 |
| YU32078B (en) | 1974-04-30 |
| BE709868A (ja) | 1968-05-30 |
| FR1568058A (ja) | 1969-05-23 |
| GB1168334A (en) | 1969-10-22 |
| FI47663C (fi) | 1974-02-11 |
| AT271491B (de) | 1969-06-10 |
| ES349741A1 (es) | 1969-04-01 |
| DE1695380A1 (de) | 1972-08-10 |
| IL29248A (en) | 1971-10-20 |
| CH471132A (fr) | 1969-04-15 |
| DK117301B (da) | 1970-04-13 |
| FR7580M (ja) | 1970-01-05 |
| FI47663B (ja) | 1973-10-31 |
| YU18468A (en) | 1973-10-31 |
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