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
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3935167 | 1967-08-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125931B true NO125931B (de) | 1972-11-27 |
Family
ID=10409082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3235/68A NO125931B (de) | 1967-08-26 | 1968-08-16 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3769295A (de) |
| JP (1) | JPS4827310B1 (de) |
| AT (1) | AT277221B (de) |
| BE (1) | BE719891A (de) |
| CA (1) | CA933926A (de) |
| CH (1) | CH502372A (de) |
| CS (1) | CS157037B2 (de) |
| DE (1) | DE1795208A1 (de) |
| DK (1) | DK118820B (de) |
| ES (1) | ES357511A1 (de) |
| FI (1) | FI48930C (de) |
| FR (2) | FR1589115A (de) |
| GB (1) | GB1234213A (de) |
| IE (1) | IE32300B1 (de) |
| NL (2) | NL6811722A (de) |
| NO (1) | NO125931B (de) |
| SE (1) | SE330540B (de) |
| YU (1) | YU199068A (de) |
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 |
| US6069141A (en) * | 1998-02-13 | 2000-05-30 | Pharmacia & Upjohn Company | Substituted aminophenyl isoxazoline derivatives useful as antimicrobials |
| JP2002504550A (ja) * | 1998-02-25 | 2002-02-12 | ファルマシア・アンド・アップジョン・カンパニー | 抗微生物剤として有用な置換アミノメチルイソオキサゾリン誘導体 |
| US6689769B2 (en) | 2000-12-21 | 2004-02-10 | Pharmacia & Upjohn Company | Antimicrobial quinolone derivatives and use of the same to treat bacterial infections |
| EP1446403B1 (de) * | 2001-10-25 | 2006-04-12 | AstraZeneca AB | Aryl substituierte oxazolidinone mit antibacterieller activität |
| WO2003035073A1 (en) * | 2001-10-25 | 2003-05-01 | 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 NL NL6811722A patent/NL6811722A/xx unknown
- 1968-08-16 NO NO3235/68A patent/NO125931B/no unknown
- 1968-08-16 SE SE11046/68A patent/SE330540B/xx unknown
- 1968-08-16 DK DK397368AA patent/DK118820B/da unknown
- 1968-08-22 CH CH1259968A patent/CH502372A/de not_active IP Right Cessation
- 1968-08-23 JP JP43059998A patent/JPS4827310B1/ja active Pending
- 1968-08-23 AT AT824568A patent/AT277221B/de not_active IP Right Cessation
- 1968-08-23 IE IE1030/68A patent/IE32300B1/xx unknown
- 1968-08-23 YU YU01990/68A patent/YU199068A/xx unknown
- 1968-08-23 BE BE719891A patent/BE719891A/xx unknown
- 1968-08-23 DE DE19681795208 patent/DE1795208A1/de active Pending
- 1968-08-23 CS CS605368A patent/CS157037B2/cs unknown
- 1968-08-23 CA CA028264A patent/CA933926A/en not_active Expired
- 1968-08-23 FR FR1589115D patent/FR1589115A/fr not_active Expired
- 1968-08-23 ES ES357511A patent/ES357511A1/es not_active Expired
- 1968-11-22 FR FR174905A patent/FR8102M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI48930B (de) | 1974-10-31 |
| CA933926A (en) | 1973-09-18 |
| IE32300B1 (en) | 1973-06-13 |
| GB1234213A (de) | 1971-06-03 |
| CH502372A (de) | 1971-01-31 |
| DE1795208A1 (de) | 1972-03-16 |
| IE32300L (en) | 1969-02-26 |
| US3769295A (en) | 1973-10-30 |
| CS157037B2 (de) | 1974-08-23 |
| BE719891A (de) | 1969-02-24 |
| NL137326C (de) | |
| FI48930C (fi) | 1975-02-10 |
| SE330540B (de) | 1970-11-23 |
| ES357511A1 (es) | 1970-03-16 |
| FR8102M (de) | 1970-07-27 |
| JPS4827310B1 (de) | 1973-08-21 |
| DK118820B (da) | 1970-10-12 |
| FR1589115A (de) | 1970-03-23 |
| AT277221B (de) | 1969-12-10 |
| NL6811722A (de) | 1969-02-28 |
| YU199068A (en) | 1978-05-15 |
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