DE2208830A1 - 3-Nitroimidazo eckige Klammer auf 1,2b eckige Klammer zu pyridazine - Google Patents
3-Nitroimidazo eckige Klammer auf 1,2b eckige Klammer zu pyridazineInfo
- Publication number
- DE2208830A1 DE2208830A1 DE19722208830 DE2208830A DE2208830A1 DE 2208830 A1 DE2208830 A1 DE 2208830A1 DE 19722208830 DE19722208830 DE 19722208830 DE 2208830 A DE2208830 A DE 2208830A DE 2208830 A1 DE2208830 A1 DE 2208830A1
- Authority
- DE
- Germany
- Prior art keywords
- pyridazine
- nitroimidazo
- radical
- group
- lower alkyl
- 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.)
- Pending
Links
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 title claims description 112
- -1 alkyl carbon Chemical compound 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- VLEORBRSFQLGDG-UHFFFAOYSA-N 3-nitro-5H-imidazo[4,5-c]pyridazine Chemical compound N1N=C([N+](=O)[O-])C=C2N=CN=C21 VLEORBRSFQLGDG-UHFFFAOYSA-N 0.000 claims 4
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- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical compound CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 description 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006749 inflammatory damage Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002350 laparotomy Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- YJRGRZJKGMBHIB-UHFFFAOYSA-N n,n-dimethyl-3-piperazin-1-ylpropan-1-amine Chemical compound CN(C)CCCN1CCNCC1 YJRGRZJKGMBHIB-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- SEGJNMCIMOLEDM-UHFFFAOYSA-N n-methyloctan-1-amine Chemical compound CCCCCCCCNC SEGJNMCIMOLEDM-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 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
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- 239000013049 sediment Substances 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
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11851071A | 1971-02-24 | 1971-02-24 | |
| US11850871A | 1971-02-24 | 1971-02-24 | |
| US13256571A | 1971-04-08 | 1971-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2208830A1 true DE2208830A1 (de) | 1972-08-31 |
Family
ID=27382178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722208830 Pending DE2208830A1 (de) | 1971-02-24 | 1972-02-24 | 3-Nitroimidazo eckige Klammer auf 1,2b eckige Klammer zu pyridazine |
Country Status (13)
| Country | Link |
|---|---|
| AR (2) | AR192343A1 (enExample) |
| BE (1) | BE779701A (enExample) |
| CH (2) | CH576473A5 (enExample) |
| DD (1) | DD96071A1 (enExample) |
| DE (1) | DE2208830A1 (enExample) |
| ES (1) | ES400141A1 (enExample) |
| FR (1) | FR2126305B1 (enExample) |
| GB (1) | GB1388915A (enExample) |
| HU (1) | HU167201B (enExample) |
| IE (1) | IE36021B1 (enExample) |
| IL (1) | IL38658A (enExample) |
| NL (1) | NL7202087A (enExample) |
| SE (1) | SE393805B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4464372A (en) * | 1982-08-16 | 1984-08-07 | Schering Corporation | Imidazo[1,2-b]pyridazines |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0717971A (ja) * | 1993-07-02 | 1995-01-20 | Takeda Chem Ind Ltd | イミダゾール誘導体、その製造法及び用途 |
-
1972
- 1972-01-25 IE IE91/72A patent/IE36021B1/xx unknown
- 1972-01-28 IL IL38658A patent/IL38658A/en unknown
- 1972-02-11 AR AR240493A patent/AR192343A1/es active
- 1972-02-17 NL NL7202087A patent/NL7202087A/xx unknown
- 1972-02-22 FR FR7205968A patent/FR2126305B1/fr not_active Expired
- 1972-02-23 HU HUAE356A patent/HU167201B/hu unknown
- 1972-02-23 SE SE7202239A patent/SE393805B/xx unknown
- 1972-02-23 BE BE779701A patent/BE779701A/xx unknown
- 1972-02-23 GB GB841772A patent/GB1388915A/en not_active Expired
- 1972-02-24 CH CH1640572*A patent/CH576473A5/xx not_active IP Right Cessation
- 1972-02-24 DD DD161109A patent/DD96071A1/xx unknown
- 1972-02-24 CH CH266572A patent/CH566337A5/xx not_active IP Right Cessation
- 1972-02-24 ES ES0400141A patent/ES400141A1/es not_active Expired
- 1972-02-24 DE DE19722208830 patent/DE2208830A1/de active Pending
- 1972-12-18 AR AR245699A patent/AR192845A1/es active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4464372A (en) * | 1982-08-16 | 1984-08-07 | Schering Corporation | Imidazo[1,2-b]pyridazines |
Also Published As
| Publication number | Publication date |
|---|---|
| CH576473A5 (enExample) | 1976-06-15 |
| ES400141A1 (es) | 1975-07-01 |
| HU167201B (enExample) | 1975-09-27 |
| BE779701A (fr) | 1972-08-23 |
| AR192343A1 (es) | 1973-02-14 |
| AR192845A1 (es) | 1973-03-14 |
| GB1388915A (en) | 1975-03-26 |
| FR2126305A1 (enExample) | 1972-10-06 |
| DD96071A1 (enExample) | 1973-03-12 |
| FR2126305B1 (enExample) | 1975-10-31 |
| IE36021L (en) | 1972-08-24 |
| IL38658A (en) | 1976-05-31 |
| IE36021B1 (en) | 1976-07-21 |
| SE393805B (sv) | 1977-05-23 |
| CH566337A5 (enExample) | 1975-09-15 |
| IL38658A0 (en) | 1972-03-28 |
| NL7202087A (enExample) | 1972-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |