NO125931B - - Google Patents
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- Publication number
- NO125931B NO125931B NO3235/68A NO323568A NO125931B NO 125931 B NO125931 B NO 125931B NO 3235/68 A NO3235/68 A NO 3235/68A NO 323568 A NO323568 A NO 323568A NO 125931 B NO125931 B NO 125931B
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- group
- nitro
- furyl
- allyl
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 25
- -1 2,3-epoxy-propoxy, morpholino, piperidino Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- AVCHVBGYOIXAQX-UHFFFAOYSA-N 3-(5-nitrofuran-2-yl)-4,5-dihydro-1,2-oxazole Chemical class [N+](=O)([O-])C1=CC=C(O1)C1=NOCC1 AVCHVBGYOIXAQX-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 40
- 239000007858 starting material Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- NVLPQIPTCCLBEU-UHFFFAOYSA-N 3-(Methylthio)-1-propene Chemical compound CSCC=C NVLPQIPTCCLBEU-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- HGBVXFNYERFTQM-UHFFFAOYSA-N 2-[3-(5-nitrofuran-2-yl)-4,5-dihydro-1,2-oxazol-5-yl]acetonitrile Chemical group O1C([N+](=O)[O-])=CC=C1C1=NOC(CC#N)C1 HGBVXFNYERFTQM-UHFFFAOYSA-N 0.000 description 1
- CKORYSXKIMYEEK-UHFFFAOYSA-N 2-cyano-N-[[3-(5-nitrofuran-2-yl)-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound C(#N)CC(=O)NCC1CC(=NO1)C=1OC(=CC1)[N+](=O)[O-] CKORYSXKIMYEEK-UHFFFAOYSA-N 0.000 description 1
- HCHJSQGMAQVHNO-UHFFFAOYSA-N 2-prop-2-enoxypropane Chemical compound CC(C)OCC=C HCHJSQGMAQVHNO-UHFFFAOYSA-N 0.000 description 1
- SUSANAYXICMXBL-UHFFFAOYSA-N 4-prop-2-enylmorpholine Chemical compound C=CCN1CCOCC1 SUSANAYXICMXBL-UHFFFAOYSA-N 0.000 description 1
- RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 230000002192 coccidiostatic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- 150000002547 isoxazolines Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DVQCXAUFUOFSDW-UHFFFAOYSA-N n-prop-2-enylacetamide Chemical compound CC(=O)NCC=C DVQCXAUFUOFSDW-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 210000001635 urinary tract Anatomy 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
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)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3935167 | 1967-08-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125931B true NO125931B (h) | 1972-11-27 |
Family
ID=10409082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3235/68A NO125931B (h) | 1967-08-26 | 1968-08-16 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3769295A (h) |
| JP (1) | JPS4827310B1 (h) |
| AT (1) | AT277221B (h) |
| BE (1) | BE719891A (h) |
| CA (1) | CA933926A (h) |
| CH (1) | CH502372A (h) |
| CS (1) | CS157037B2 (h) |
| DE (1) | DE1795208A1 (h) |
| DK (1) | DK118820B (h) |
| ES (1) | ES357511A1 (h) |
| FI (1) | FI48930C (h) |
| FR (2) | FR1589115A (h) |
| GB (1) | GB1234213A (h) |
| IE (1) | IE32300B1 (h) |
| NL (2) | NL6811722A (h) |
| NO (1) | NO125931B (h) |
| SE (1) | SE330540B (h) |
| YU (1) | YU199068A (h) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3915978A (en) * | 1970-01-07 | 1975-10-28 | Merck & Co Inc | Nitroimidazoles |
| US4010176A (en) * | 1972-10-27 | 1977-03-01 | Merck & Co., Inc. | Isoxazole substituted nitroimidazoles |
| US4109002A (en) * | 1976-06-14 | 1978-08-22 | Eli Lilly And Company | Fungicidal 3-phenyl-5-(substituted methyl) isoxaxoles |
| US4203994A (en) * | 1976-06-14 | 1980-05-20 | Eli Lilly And Company | Fungicidal 3-phenyl-5-(substituted methyl)isoxazoles |
| IL85691A0 (en) * | 1987-04-10 | 1988-08-31 | Pennwalt Corp | 5-(phenyl or phenoxymethyl)-3-(2-furanyl or 2-thienyl)-3-(1h-imidazol-1-ylmethyl)-2-methylisoxazolidines and salts thereof |
| ATE227277T1 (de) * | 1996-08-21 | 2002-11-15 | Upjohn Co | Isoxazoline derivate und ihre verwendung als antimikroben |
| AU757197B2 (en) * | 1998-02-13 | 2003-02-06 | Pharmacia & Upjohn Company | Substituted aminophenyl isoxazoline derivatives useful as antimicrobials |
| AU3180999A (en) * | 1998-02-25 | 1999-09-15 | Pharmacia & Upjohn Company | Substituted aminomethyl isoxazoline derivatives useful as antimicrobials |
| WO2002059116A2 (en) | 2000-12-21 | 2002-08-01 | Pharmacia & Upjohn Company | Antimicrobial quinolone derivatives and use of the same to treat bacterial infections |
| DE60210654T2 (de) * | 2001-10-25 | 2007-01-25 | Astrazeneca Ab | Aryl substituierte oxazolidinone mit antibacterieller activität |
| EP1443930A1 (en) * | 2001-10-25 | 2004-08-11 | AstraZeneca AB | Isoxazoline derivatives useful as antimicrobials |
| CN101774976B (zh) * | 2010-01-26 | 2012-05-09 | 天津药物研究院 | 磺酰基异噁唑啉衍生物及抗肿瘤用途 |
| CN101781294B (zh) * | 2010-03-10 | 2012-02-01 | 天津药物研究院 | 一类咪唑的衍生物、其制备方法和用途 |
| CN107709335B (zh) * | 2015-02-27 | 2022-05-31 | 海洋规划生物工厂株式会社 | Kakeromycin及其衍生物的制造方法 |
-
0
- NL NL137326D patent/NL137326C/xx active
-
1967
- 1967-08-26 GB GB3935167A patent/GB1234213A/en not_active Expired
-
1968
- 1968-08-09 FI FI682252A patent/FI48930C/fi active
- 1968-08-14 US US00752479A patent/US3769295A/en not_active Expired - Lifetime
- 1968-08-16 DK DK397368AA patent/DK118820B/da unknown
- 1968-08-16 NL NL6811722A patent/NL6811722A/xx unknown
- 1968-08-16 SE SE11046/68A patent/SE330540B/xx unknown
- 1968-08-16 NO NO3235/68A patent/NO125931B/no unknown
- 1968-08-22 CH CH1259968A patent/CH502372A/de not_active IP Right Cessation
- 1968-08-23 DE DE19681795208 patent/DE1795208A1/de active Pending
- 1968-08-23 JP JP43059998A patent/JPS4827310B1/ja active Pending
- 1968-08-23 ES ES357511A patent/ES357511A1/es not_active Expired
- 1968-08-23 YU YU01990/68A patent/YU199068A/xx unknown
- 1968-08-23 FR FR1589115D patent/FR1589115A/fr not_active Expired
- 1968-08-23 CS CS605368A patent/CS157037B2/cs unknown
- 1968-08-23 BE BE719891A patent/BE719891A/xx unknown
- 1968-08-23 AT AT824568A patent/AT277221B/de not_active IP Right Cessation
- 1968-08-23 CA CA028264A patent/CA933926A/en not_active Expired
- 1968-08-23 IE IE1030/68A patent/IE32300B1/xx unknown
- 1968-11-22 FR FR174905A patent/FR8102M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1234213A (h) | 1971-06-03 |
| BE719891A (h) | 1969-02-24 |
| NL137326C (h) | |
| NL6811722A (h) | 1969-02-28 |
| FI48930C (fi) | 1975-02-10 |
| ES357511A1 (es) | 1970-03-16 |
| FI48930B (h) | 1974-10-31 |
| SE330540B (h) | 1970-11-23 |
| DE1795208A1 (de) | 1972-03-16 |
| FR8102M (h) | 1970-07-27 |
| US3769295A (en) | 1973-10-30 |
| FR1589115A (h) | 1970-03-23 |
| IE32300B1 (en) | 1973-06-13 |
| DK118820B (da) | 1970-10-12 |
| IE32300L (en) | 1969-02-26 |
| YU199068A (en) | 1978-05-15 |
| JPS4827310B1 (h) | 1973-08-21 |
| CS157037B2 (h) | 1974-08-23 |
| AT277221B (de) | 1969-12-10 |
| CA933926A (en) | 1973-09-18 |
| CH502372A (de) | 1971-01-31 |
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