NO803735L - 6-(pyridinyl)pyridaziner og fremgangsmaate til deres fremstilling - Google Patents
6-(pyridinyl)pyridaziner og fremgangsmaate til deres fremstillingInfo
- Publication number
- NO803735L NO803735L NO803735A NO803735A NO803735L NO 803735 L NO803735 L NO 803735L NO 803735 A NO803735 A NO 803735A NO 803735 A NO803735 A NO 803735A NO 803735 L NO803735 L NO 803735L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- pyridazine
- acid
- chloro
- hydrazino
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 20
- FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical class [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 title 1
- 150000004892 pyridazines Chemical class 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 30
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- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- ZFKNPROCZUOLMY-UHFFFAOYSA-N 3-chloro-6-pyridin-4-ylpyridazine Chemical compound N1=NC(Cl)=CC=C1C1=CC=NC=C1 ZFKNPROCZUOLMY-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 2
- -1 4-pyridinyl Chemical group 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
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- 238000006243 chemical reaction Methods 0.000 description 10
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- 230000000747 cardiac effect Effects 0.000 description 8
- FBOQGQULUAPQCC-UHFFFAOYSA-N 3-pyridin-4-yl-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C=2C=CN=CC=2)=N1 FBOQGQULUAPQCC-UHFFFAOYSA-N 0.000 description 7
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- 239000000543 intermediate Substances 0.000 description 6
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
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- 150000007513 acids Chemical class 0.000 description 3
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- 230000003177 cardiotonic effect Effects 0.000 description 3
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- 238000001816 cooling Methods 0.000 description 3
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- 230000000144 pharmacologic effect Effects 0.000 description 3
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 2
- YUNWXAGTTHZGPB-UHFFFAOYSA-N 3-(2,6-dimethylpyridin-4-yl)-1h-pyridazin-6-one Chemical compound CC1=NC(C)=CC(C2=NNC(=O)C=C2)=C1 YUNWXAGTTHZGPB-UHFFFAOYSA-N 0.000 description 2
- QSZSECGVFAOGHT-UHFFFAOYSA-N 3-(2-methylpyridin-3-yl)-1h-pyridazin-6-one Chemical compound CC1=NC=CC=C1C1=CC=C(O)N=N1 QSZSECGVFAOGHT-UHFFFAOYSA-N 0.000 description 2
- AYJCYJJVFFRRAF-UHFFFAOYSA-N 3-(3-ethylpyridin-4-yl)-1h-pyridazin-6-one Chemical compound CCC1=CN=CC=C1C1=NNC(=O)C=C1 AYJCYJJVFFRRAF-UHFFFAOYSA-N 0.000 description 2
- PWKDVSFTKHEPKK-UHFFFAOYSA-N 3-(5-methylpyridin-3-yl)-1h-pyridazin-6-one Chemical compound CC1=CN=CC(C2=NNC(=O)C=C2)=C1 PWKDVSFTKHEPKK-UHFFFAOYSA-N 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- ZGCHATBSUIJLRL-UHFFFAOYSA-N hydrazine sulfate Chemical compound NN.OS(O)(=O)=O ZGCHATBSUIJLRL-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000000936 membranestabilizing effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10319279A | 1979-12-13 | 1979-12-13 | |
| US06/173,004 US4304775A (en) | 1979-12-13 | 1980-07-28 | 3-Hydrazino-6-(pyridinyl) pyridazines and cardiotonic use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO803735L true NO803735L (no) | 1981-06-15 |
Family
ID=26800173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO803735A NO803735L (no) | 1979-12-13 | 1980-12-11 | 6-(pyridinyl)pyridaziner og fremgangsmaate til deres fremstilling |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4304775A (de) |
| KR (1) | KR830004290A (de) |
| AU (1) | AU6515780A (de) |
| DE (1) | DE3046914A1 (de) |
| DK (1) | DK531880A (de) |
| FI (1) | FI803776L (de) |
| FR (2) | FR2471380A1 (de) |
| GB (1) | GB2066241A (de) |
| IL (1) | IL61626A0 (de) |
| IT (1) | IT1134684B (de) |
| LU (1) | LU82997A1 (de) |
| NL (1) | NL8006658A (de) |
| NO (1) | NO803735L (de) |
| PT (1) | PT72159B (de) |
| SE (1) | SE8008731L (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4590194A (en) * | 1981-10-05 | 1986-05-20 | Sterling Drug Inc. | 3-[methyl or dimethyl)amino]-6-(pyridinyl)pyridazines and their cardiotonic use |
| US4432979A (en) * | 1981-10-26 | 1984-02-21 | William H. Rorer, Inc. | Pyridone compounds |
| US4514400A (en) * | 1981-10-26 | 1985-04-30 | William H. Rorer, Inc. | Cardiotonic 5-heteroaryl-pyridone |
| US5001125A (en) * | 1984-03-26 | 1991-03-19 | Janssen Pharmaceutica N.V. | Anti-virally active pyridazinamines |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3717365A (en) * | 1970-10-19 | 1973-02-20 | Cochran Western Corp | Automatic vehicle hitch assembly |
| US4072746A (en) * | 1975-10-14 | 1978-02-07 | Sterling Drug Inc. | 3-Amino-5-(pyridinyl)-2(1H)-pyridinones |
| IT1063908B (it) * | 1976-06-11 | 1985-02-18 | Isf Spa | Derivati idrazinopiridazinici |
| HU176100B (en) * | 1977-10-25 | 1980-12-28 | Gyogyszerkutato Intezet | Process for preparing new 3-/1-pyrazolyl/-pyridazine derivatives |
-
1980
- 1980-07-28 US US06/173,004 patent/US4304775A/en not_active Expired - Lifetime
- 1980-11-28 GB GB8038185A patent/GB2066241A/en not_active Withdrawn
- 1980-12-03 IL IL61626A patent/IL61626A0/xx unknown
- 1980-12-04 FI FI803776A patent/FI803776L/fi not_active Application Discontinuation
- 1980-12-04 PT PT72159A patent/PT72159B/pt unknown
- 1980-12-08 AU AU65157/80A patent/AU6515780A/en not_active Abandoned
- 1980-12-08 NL NL8006658A patent/NL8006658A/nl not_active Application Discontinuation
- 1980-12-09 FR FR8026091A patent/FR2471380A1/fr not_active Withdrawn
- 1980-12-11 IT IT26581/80A patent/IT1134684B/it active
- 1980-12-11 SE SE8008731A patent/SE8008731L/xx not_active Application Discontinuation
- 1980-12-11 NO NO803735A patent/NO803735L/no unknown
- 1980-12-12 DK DK531880A patent/DK531880A/da unknown
- 1980-12-12 LU LU82997A patent/LU82997A1/fr unknown
- 1980-12-12 DE DE19803046914 patent/DE3046914A1/de not_active Withdrawn
- 1980-12-12 KR KR1019800004721A patent/KR830004290A/ko unknown
-
1981
- 1981-06-11 FR FR8111507A patent/FR2479826A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| PT72159B (en) | 1981-10-28 |
| IL61626A0 (en) | 1981-01-30 |
| LU82997A1 (fr) | 1981-07-23 |
| US4304775A (en) | 1981-12-08 |
| FI803776L (fi) | 1981-06-14 |
| NL8006658A (nl) | 1981-07-16 |
| AU6515780A (en) | 1981-06-18 |
| FR2471380A1 (fr) | 1981-06-19 |
| SE8008731L (sv) | 1981-06-14 |
| DE3046914A1 (de) | 1981-09-17 |
| DK531880A (da) | 1981-06-14 |
| FR2479826A1 (fr) | 1981-10-09 |
| IT1134684B (it) | 1986-08-13 |
| PT72159A (en) | 1981-01-01 |
| IT8026581A0 (it) | 1980-12-11 |
| KR830004290A (ko) | 1983-07-09 |
| GB2066241A (en) | 1981-07-08 |
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