SE441923B - 1-acyl-2-imidazolin till anvendning som mellanprodukt vid framstellning av 1-osubstituerad-2-imidazolin samt forfarande for dess framstellning - Google Patents
1-acyl-2-imidazolin till anvendning som mellanprodukt vid framstellning av 1-osubstituerad-2-imidazolin samt forfarande for dess framstellningInfo
- Publication number
- SE441923B SE441923B SE7712786A SE7712786A SE441923B SE 441923 B SE441923 B SE 441923B SE 7712786 A SE7712786 A SE 7712786A SE 7712786 A SE7712786 A SE 7712786A SE 441923 B SE441923 B SE 441923B
- Authority
- SE
- Sweden
- Prior art keywords
- imidazoline
- indanylamino
- acyl
- preparation
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- WGCQZEQXKNFPJL-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound CC(=O)N1CCN=C1NC1=CC=CC2=C1CCC2 WGCQZEQXKNFPJL-UHFFFAOYSA-N 0.000 claims description 3
- JGTRKYPDNSKJAT-UHFFFAOYSA-N 1-[2-(5,6,7,8-tetrahydronaphthalen-1-ylamino)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound CC(=O)N1CCN=C1NC1=CC=CC2=C1CCCC2 JGTRKYPDNSKJAT-UHFFFAOYSA-N 0.000 claims description 2
- IUVCBSZCGJAZNU-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-phenylmethanone Chemical group C1CN=C(NC=2C=3CCCC=3C=CC=2)N1C(=O)C1=CC=CC=C1 IUVCBSZCGJAZNU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- IRLMWBRTASRHRA-UHFFFAOYSA-N ethyl 2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazole-1-carboxylate Chemical group CCOC(=O)N1CCN=C1NC1=CC=CC2=C1CCC2 IRLMWBRTASRHRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- -1 carboxylic acid halides Chemical class 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- RXTJLDXSGNEJIT-UHFFFAOYSA-N 2,3-dihydro-1h-inden-4-amine Chemical compound NC1=CC=CC2=C1CCC2 RXTJLDXSGNEJIT-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 8
- 229910002651 NO3 Inorganic materials 0.000 description 6
- 238000005947 deacylation reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- SODWJACROGQSMM-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-amine Chemical compound C1CCCC2=C1C=CC=C2N SODWJACROGQSMM-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000020176 deacylation Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JJWACYUTERPMBM-UHFFFAOYSA-N 1-acetylimidazolidin-2-one Chemical compound CC(=O)N1CCNC1=O JJWACYUTERPMBM-UHFFFAOYSA-N 0.000 description 2
- AJSFBSYWKIBTGP-UHFFFAOYSA-N 1-benzoylimidazolidin-2-one Chemical compound C=1C=CC=CC=1C(=O)N1CCNC1=O AJSFBSYWKIBTGP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- CNKLAMCYSQDBMF-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-4-yl)-4,5-dihydro-1h-imidazol-2-amine;nitric acid Chemical compound O[N+]([O-])=O.C=12CCCC2=CC=CC=1NC1=NCCN1 CNKLAMCYSQDBMF-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YOLPDJLHLIZAQT-UHFFFAOYSA-N (4-chlorophenyl)-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 YOLPDJLHLIZAQT-UHFFFAOYSA-N 0.000 description 1
- FRLKFEIYNBWACZ-UHFFFAOYSA-N (4-methylphenyl)-[2-(5,6,7,8-tetrahydronaphthalen-1-ylamino)-4,5-dihydroimidazol-1-yl]methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(NC=2C=3CCCCC=3C=CC=2)=NCC1 FRLKFEIYNBWACZ-UHFFFAOYSA-N 0.000 description 1
- WVVVGUCAFMYDSL-UHFFFAOYSA-N 1-(1,3-benzodioxole-5-carbonyl)imidazolidin-2-one Chemical compound C=1C=C2OCOC2=CC=1C(=O)N1CCNC1=O WVVVGUCAFMYDSL-UHFFFAOYSA-N 0.000 description 1
- ACUWFQYXVZLYSM-UHFFFAOYSA-N 1-(2,2,2-trifluoroacetyl)imidazolidin-2-one Chemical compound FC(F)(F)C(=O)N1CCNC1=O ACUWFQYXVZLYSM-UHFFFAOYSA-N 0.000 description 1
- DPTZKHGTKQXUOZ-UHFFFAOYSA-N 1-(2-chlorobenzoyl)imidazolidin-2-one Chemical compound ClC1=CC=CC=C1C(=O)N1C(=O)NCC1 DPTZKHGTKQXUOZ-UHFFFAOYSA-N 0.000 description 1
- MPDAZEGQKSMGOX-UHFFFAOYSA-N 1-(3,4-dimethoxybenzoyl)imidazolidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)N1C(=O)NCC1 MPDAZEGQKSMGOX-UHFFFAOYSA-N 0.000 description 1
- BTROLKJFQYVFFC-UHFFFAOYSA-N 1-(3-chlorobenzoyl)imidazolidin-2-one Chemical compound ClC1=CC=CC(C(=O)N2C(NCC2)=O)=C1 BTROLKJFQYVFFC-UHFFFAOYSA-N 0.000 description 1
- SSYOLUIBSVWNAX-UHFFFAOYSA-N 1-(3-phenylprop-2-enoyl)imidazolidin-2-one Chemical compound C1CNC(=O)N1C(=O)C=CC1=CC=CC=C1 SSYOLUIBSVWNAX-UHFFFAOYSA-N 0.000 description 1
- DMWJSNYHOZRFEK-UHFFFAOYSA-N 1-(4-chlorobenzoyl)imidazolidin-2-one Chemical compound C1=CC(Cl)=CC=C1C(=O)N1C(=O)NCC1 DMWJSNYHOZRFEK-UHFFFAOYSA-N 0.000 description 1
- WGAVFSJWEYTCGK-UHFFFAOYSA-N 1-(4-ethoxybenzoyl)imidazolidin-2-one Chemical compound C1=CC(OCC)=CC=C1C(=O)N1C(=O)NCC1 WGAVFSJWEYTCGK-UHFFFAOYSA-N 0.000 description 1
- PHAXGRPLSGRXAE-UHFFFAOYSA-N 1-(4-fluorobenzoyl)imidazolidin-2-one Chemical compound C1=CC(F)=CC=C1C(=O)N1C(=O)NCC1 PHAXGRPLSGRXAE-UHFFFAOYSA-N 0.000 description 1
- AFWMHNPVEWFLHA-UHFFFAOYSA-N 1-(4-methylbenzoyl)imidazolidin-2-one Chemical compound C1=CC(C)=CC=C1C(=O)N1C(=O)NCC1 AFWMHNPVEWFLHA-UHFFFAOYSA-N 0.000 description 1
- YGNBUIITRUOKCC-UHFFFAOYSA-N 1-(4-propan-2-ylbenzoyl)imidazolidin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(=O)N1C(=O)NCC1 YGNBUIITRUOKCC-UHFFFAOYSA-N 0.000 description 1
- TWFHWUYDTLKJKG-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-2-(2-methylphenyl)ethanone Chemical compound CC1=CC=CC=C1CC(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 TWFHWUYDTLKJKG-UHFFFAOYSA-N 0.000 description 1
- UVBDUZIFCYSXTR-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-2-phenylpropan-1-one Chemical compound C1CN=C(NC=2C=3CCCC=3C=CC=2)N1C(=O)C(C)C1=CC=CC=C1 UVBDUZIFCYSXTR-UHFFFAOYSA-N 0.000 description 1
- JOCWWLNUKYYVEV-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]propan-1-one Chemical compound CCC(=O)N1CCN=C1NC1=CC=CC2=C1CCC2 JOCWWLNUKYYVEV-UHFFFAOYSA-N 0.000 description 1
- MPSSSVUOOMDBRF-UHFFFAOYSA-N 1-propanoylimidazolidin-2-one Chemical compound CCC(=O)N1CCNC1=O MPSSSVUOOMDBRF-UHFFFAOYSA-N 0.000 description 1
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 1
- SIJHZZKGVGHIQC-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound C=1C=C2OCCOC2=CC=1CC(=O)N1CCN=C1NC1=CC=CC2=C1CCC2 SIJHZZKGVGHIQC-UHFFFAOYSA-N 0.000 description 1
- OBOWRLLQPAECAX-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]propan-1-one Chemical compound C1CN=C(NC=2C=3CCCC=3C=CC=2)N1C(=O)C(C)C1=CC=C(Cl)C=C1 OBOWRLLQPAECAX-UHFFFAOYSA-N 0.000 description 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
- TUFDCXJCUGHIJH-UHFFFAOYSA-N 2-oxoimidazolidine-1-carbaldehyde Chemical compound O=CN1CCNC1=O TUFDCXJCUGHIJH-UHFFFAOYSA-N 0.000 description 1
- ZHTHFRIQYSIAOF-UHFFFAOYSA-N 4,5-dihydro-1h-imidazole;nitric acid Chemical compound O[N+]([O-])=O.C1CN=CN1 ZHTHFRIQYSIAOF-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- IWSOCBAISYFGJW-UHFFFAOYSA-N N-(2,3-dihydro-1H-inden-1-yl)-4,5-dihydro-1H-imidazol-5-amine Chemical compound C1(CCC2=CC=CC=C12)NC1N=CNC1 IWSOCBAISYFGJW-UHFFFAOYSA-N 0.000 description 1
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- STWPQMMPUXKPIY-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-1-ylamino)-4,5-dihydroimidazol-1-yl]-phenylmethanone Chemical compound C1CN=C(NC2C3=CC=CC=C3CC2)N1C(=O)C1=CC=CC=C1 STWPQMMPUXKPIY-UHFFFAOYSA-N 0.000 description 1
- LKDQOEAGAJYEQR-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-(2,6-dimethylphenyl)methanone Chemical compound CC1=CC=CC(C)=C1C(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 LKDQOEAGAJYEQR-UHFFFAOYSA-N 0.000 description 1
- ZAWIAMCXQZMVGO-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2C(=NCC2)NC=2C=3CCCC=3C=CC=2)=C1 ZAWIAMCXQZMVGO-UHFFFAOYSA-N 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- QQJLHRRUATVHED-UHFFFAOYSA-N tramazoline Chemical compound N1CCN=C1NC1=CC=CC2=C1CCCC2 QQJLHRRUATVHED-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2652004A DE2652004C3 (de) | 1976-11-15 | 1976-11-15 | l-Acyl-2-arylamino-2-imidazoline, Verfahren zu ihrer Herstellung und ihre Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7712786L SE7712786L (sv) | 1978-05-16 |
| SE441923B true SE441923B (sv) | 1985-11-18 |
Family
ID=5993186
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7712786A SE441923B (sv) | 1976-11-15 | 1977-11-11 | 1-acyl-2-imidazolin till anvendning som mellanprodukt vid framstellning av 1-osubstituerad-2-imidazolin samt forfarande for dess framstellning |
| SE8205383A SE455502B (sv) | 1976-11-15 | 1982-09-20 | Forfarande for deacylering av 1-acyl-2-imidazolin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8205383A SE455502B (sv) | 1976-11-15 | 1982-09-20 | Forfarande for deacylering av 1-acyl-2-imidazolin |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4269990A (enExample) |
| AT (1) | AT362786B (enExample) |
| CA (1) | CA1099274A (enExample) |
| CH (1) | CH633274A5 (enExample) |
| DE (1) | DE2652004C3 (enExample) |
| FR (1) | FR2370736A1 (enExample) |
| GB (1) | GB1591879A (enExample) |
| NL (1) | NL7712149A (enExample) |
| SE (2) | SE441923B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3011327A1 (de) * | 1980-03-24 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | 1-aroyl-2-phenylamino-2-imidazoline, ihre herstellung und verwendung |
| US6670364B2 (en) * | 2001-01-31 | 2003-12-30 | Telik, Inc. | Antagonists of MCP-1 function and methods of use thereof |
| US6962926B2 (en) * | 2001-01-31 | 2005-11-08 | Telik, Inc. | Antagonist of MCP-1 function, and compositions and methods of use thereof |
| TWI245761B (en) | 2001-03-01 | 2005-12-21 | Telik Inc | Antagonists of MCP-1 function and methods of use thereof |
| TWI236474B (en) * | 2001-04-03 | 2005-07-21 | Telik Inc | Antagonists of MCP-1 function and methods of use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3288805A (en) * | 1966-11-29 | Amino-eviid azoline | ||
| US3636219A (en) * | 1964-03-02 | 1972-01-18 | Du Pont | Anticholinergic compositions containing certain thiazolines or imidazolines |
| CH488188A (de) * | 1968-11-08 | 1970-03-31 | Zellweger Uster Ag | Fadenklemme für Fadenprüfmaschinen |
| BE741947A (en) | 1969-11-19 | 1970-05-04 | N-acyl-2-arylamino-imidazoline | |
| DE2316377C3 (de) * | 1973-04-02 | 1978-11-02 | Lentia Gmbh, Chem. U. Pharm. Erzeugnisse - Industriebedarf, 8000 Muenchen | Verfahren zur Herstellung von 2-Phenyl-amino-2-imidazolin-Derivaten und von deren Salzen |
| AT330769B (de) * | 1974-04-05 | 1976-07-26 | Chemie Linz Ag | Verfahren zur herstellung von 2-arylamino- 2-imidazolin-derivaten und ihren salzen |
-
1976
- 1976-11-15 DE DE2652004A patent/DE2652004C3/de not_active Expired
-
1977
- 1977-11-03 NL NL7712149A patent/NL7712149A/xx not_active Application Discontinuation
- 1977-11-11 SE SE7712786A patent/SE441923B/sv not_active IP Right Cessation
- 1977-11-14 GB GB47237/77A patent/GB1591879A/en not_active Expired
- 1977-11-14 CH CH1387777A patent/CH633274A5/de not_active IP Right Cessation
- 1977-11-14 CA CA290,841A patent/CA1099274A/en not_active Expired
- 1977-11-14 AT AT0811577A patent/AT362786B/de not_active IP Right Cessation
- 1977-11-15 FR FR7734256A patent/FR2370736A1/fr active Granted
-
1979
- 1979-12-05 US US06/100,655 patent/US4269990A/en not_active Expired - Lifetime
-
1982
- 1982-09-20 SE SE8205383A patent/SE455502B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2652004B2 (de) | 1979-01-18 |
| SE455502B (sv) | 1988-07-18 |
| DE2652004A1 (de) | 1978-05-24 |
| CH633274A5 (de) | 1982-11-30 |
| DE2652004C3 (de) | 1979-09-13 |
| NL7712149A (nl) | 1978-05-17 |
| SE8205383D0 (sv) | 1982-09-20 |
| CA1099274A (en) | 1981-04-14 |
| AT362786B (de) | 1981-06-10 |
| ATA811577A (de) | 1980-11-15 |
| FR2370736A1 (fr) | 1978-06-09 |
| SE8205383L (sv) | 1982-09-20 |
| FR2370736B1 (enExample) | 1980-12-19 |
| GB1591879A (en) | 1981-07-01 |
| SE7712786L (sv) | 1978-05-16 |
| US4269990A (en) | 1981-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 7712786-8 Effective date: 19940610 Format of ref document f/p: F |