CH616659A5 - - Google Patents
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- Publication number
- CH616659A5 CH616659A5 CH1183076A CH1183076A CH616659A5 CH 616659 A5 CH616659 A5 CH 616659A5 CH 1183076 A CH1183076 A CH 1183076A CH 1183076 A CH1183076 A CH 1183076A CH 616659 A5 CH616659 A5 CH 616659A5
- Authority
- CH
- Switzerland
- Prior art keywords
- diphenyl
- formula
- pyrrolidinone
- compound
- preparation
- Prior art date
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 230000017105 transposition Effects 0.000 claims description 4
- HJVHZBRVMIZBPH-UHFFFAOYSA-N 4-(chloromethyl)-3,3-diphenyl-1-propan-2-ylpyrrolidin-2-one Chemical compound O=C1N(C(C)C)CC(CCl)C1(C=1C=CC=CC=1)C1=CC=CC=C1 HJVHZBRVMIZBPH-UHFFFAOYSA-N 0.000 claims description 3
- KTOFYLXSANIPND-UHFFFAOYSA-N 4-(hydroxymethyl)pyrrolidin-2-one Chemical compound OCC1CNC(=O)C1 KTOFYLXSANIPND-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 2
- 235000009518 sodium iodide Nutrition 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical class CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 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 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 α-methylbenzyl Chemical group 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- IAMSQROJFTYWGK-UHFFFAOYSA-N 3,3-diphenyl-4-[(propan-2-ylamino)methyl]oxolan-2-one Chemical compound CC(C)NCC1COC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 IAMSQROJFTYWGK-UHFFFAOYSA-N 0.000 description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- KMDKDQXWHWLFKP-UHFFFAOYSA-N 4-(hydroxymethyl)-3,3-diphenyl-1-propan-2-ylpyrrolidin-2-one Chemical compound O=C1N(C(C)C)CC(CO)C1(C=1C=CC=CC=1)C1=CC=CC=C1 KMDKDQXWHWLFKP-UHFFFAOYSA-N 0.000 description 2
- VNAGWSKMCITODC-UHFFFAOYSA-N 4-[4-(7-hydroxyheptoxy)phenyl]benzonitrile Chemical compound C1=CC(OCCCCCCCO)=CC=C1C1=CC=C(C#N)C=C1 VNAGWSKMCITODC-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- XMYVPFWEJAQKHB-UHFFFAOYSA-N (1-propan-2-ylazetidin-3-yl) methanesulfonate Chemical compound CC(C)N1CC(OS(C)(=O)=O)C1 XMYVPFWEJAQKHB-UHFFFAOYSA-N 0.000 description 1
- DDZSUTRMRFPSGB-UHFFFAOYSA-N 1-butyl-4-(hydroxymethyl)-3,3-diphenylpyrrolidin-2-one Chemical compound O=C1N(CCCC)CC(CO)C1(C=1C=CC=CC=1)C1=CC=CC=C1 DDZSUTRMRFPSGB-UHFFFAOYSA-N 0.000 description 1
- ATAIUNWIGWTQJI-UHFFFAOYSA-N 1-ethyl-4-(hydroxymethyl)-3,3-diphenylpyrrolidin-2-one Chemical compound O=C1N(CC)CC(CO)C1(C=1C=CC=CC=1)C1=CC=CC=C1 ATAIUNWIGWTQJI-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical class C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- JLMICLBCMAGHFI-UHFFFAOYSA-N 3,3-diphenyl-1-propan-2-ylpyrrolidin-2-one Chemical compound O=C1N(C(C)C)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 JLMICLBCMAGHFI-UHFFFAOYSA-N 0.000 description 1
- WXKCTFWSGGKULR-UHFFFAOYSA-N 3-chloro-1-methylazetidine Chemical compound CN1CC(Cl)C1 WXKCTFWSGGKULR-UHFFFAOYSA-N 0.000 description 1
- WPGKLOSHILQAQK-UHFFFAOYSA-N 4-(hydroxymethyl)-1-methyl-3,3-diphenylpyrrolidin-2-one Chemical compound O=C1N(C)CC(CO)C1(C=1C=CC=CC=1)C1=CC=CC=C1 WPGKLOSHILQAQK-UHFFFAOYSA-N 0.000 description 1
- RYBKMPHHGYJSAX-UHFFFAOYSA-N 4-(hydroxymethyl)-3,3-diphenyl-1-(1-phenylethyl)pyrrolidin-2-one Chemical compound C=1C=CC=CC=1C(C)N(C1=O)CC(CO)C1(C=1C=CC=CC=1)C1=CC=CC=C1 RYBKMPHHGYJSAX-UHFFFAOYSA-N 0.000 description 1
- OKQVHLJKFZNEAO-UHFFFAOYSA-N 4-(hydroxymethyl)-3,3-diphenyl-1-propylpyrrolidin-2-one Chemical compound O=C1N(CCC)CC(CO)C1(C=1C=CC=CC=1)C1=CC=CC=C1 OKQVHLJKFZNEAO-UHFFFAOYSA-N 0.000 description 1
- YEWGIGCYIAMFMA-UHFFFAOYSA-N LSM-2007 Chemical compound C1C2=CC=CC=C2CCN(C)CCC2=C1NC1=CC=CC=C21 YEWGIGCYIAMFMA-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001142 anti-diarrhea Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical class OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 description 1
- 125000006543 azetidinylalkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 150000003953 γ-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/615,951 US4119637A (en) | 1975-09-23 | 1975-09-23 | 4-Hydroxymethyl-2-pyrrolidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616659A5 true CH616659A5 (d) | 1980-04-15 |
Family
ID=24467444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1183076A CH616659A5 (d) | 1975-09-23 | 1976-09-17 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4119637A (d) |
| JP (2) | JPS6059228B2 (d) |
| AU (2) | AU512445B2 (d) |
| BE (1) | BE846402A (d) |
| BR (1) | BR7606209A (d) |
| CA (1) | CA1077497A (d) |
| CH (1) | CH616659A5 (d) |
| DE (2) | DE2661028C2 (d) |
| DK (1) | DK160548C (d) |
| ES (2) | ES451752A1 (d) |
| FI (1) | FI67370C (d) |
| FR (2) | FR2333792A1 (d) |
| GB (2) | GB1552687A (d) |
| IE (1) | IE44843B1 (d) |
| IL (1) | IL50436A (d) |
| MX (1) | MX3846E (d) |
| NL (1) | NL7610526A (d) |
| PH (1) | PH13940A (d) |
| PT (1) | PT65624B (d) |
| SE (1) | SE418397B (d) |
| ZA (1) | ZA765417B (d) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4133881A (en) * | 1977-04-27 | 1979-01-09 | A. H. Robins Company, Incorporated | Azetidinyl acetonitrile and acetamide antiarrhythmia compositions and methods |
| DE3326724A1 (de) * | 1983-07-25 | 1985-02-07 | Boehringer Ingelheim KG, 6507 Ingelheim | In 1-stellung substituierte 4-hydroxymethyl-pyrrolidinone, verfahren zu ihrer herstellung, pharmazeutische zusammensetzungen und zwischenprodukte |
| GB8419085D0 (en) * | 1984-07-26 | 1984-08-30 | Shell Int Research | Azetidine derivatives |
| DE3537075A1 (de) * | 1985-10-18 | 1987-04-23 | Bayer Ag | Verfahren zur herstellung von clausenamid |
| DE3823299A1 (de) * | 1988-07-07 | 1990-01-11 | Schering Ag | Substituierte phenyl-pyrrolidin-2-one, -oxazolidin-2-one und -imidazolidin-2-one, ihre herstellung sowie verwendung in arzneimitteln |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2650231A (en) * | 1949-11-19 | 1953-08-25 | Smith Kline French Lab | Aminovalerolactones and method for their production |
| JPS5422973B2 (d) * | 1972-03-17 | 1979-08-10 | ||
| FR2235685A1 (en) * | 1973-06-20 | 1975-01-31 | Ugine Kuhlmann | 1-Amino alkyl-3,3-diphenyl-2-pyrrolidinones - useful as coronary dilators, anti histamines choleretics etc. |
| ES442233A1 (es) * | 1974-11-06 | 1977-07-01 | Hoechst Ag | Procedimiento para la preparacion de pirrolidonas. |
-
1975
- 1975-09-23 US US05/615,951 patent/US4119637A/en not_active Expired - Lifetime
-
1976
- 1976-09-08 IL IL50436A patent/IL50436A/xx unknown
- 1976-09-09 ZA ZA765417A patent/ZA765417B/xx unknown
- 1976-09-15 PH PH18910A patent/PH13940A/en unknown
- 1976-09-17 CH CH1183076A patent/CH616659A5/fr not_active IP Right Cessation
- 1976-09-17 SE SE7610362A patent/SE418397B/xx not_active IP Right Cessation
- 1976-09-20 BR BR7606209A patent/BR7606209A/pt unknown
- 1976-09-21 CA CA261,718A patent/CA1077497A/en not_active Expired
- 1976-09-21 GB GB234/79A patent/GB1552687A/en not_active Expired
- 1976-09-21 BE BE170788A patent/BE846402A/xx not_active IP Right Cessation
- 1976-09-21 FI FI762694A patent/FI67370C/fi not_active IP Right Cessation
- 1976-09-21 FR FR7628327A patent/FR2333792A1/fr active Granted
- 1976-09-21 MX MX764936U patent/MX3846E/es unknown
- 1976-09-21 IE IE2085/76A patent/IE44843B1/en unknown
- 1976-09-21 GB GB39125/76A patent/GB1552686A/en not_active Expired
- 1976-09-22 ES ES451752A patent/ES451752A1/es not_active Expired
- 1976-09-22 NL NL7610526A patent/NL7610526A/xx not_active Application Discontinuation
- 1976-09-22 DE DE2661028A patent/DE2661028C2/de not_active Expired
- 1976-09-22 DK DK426376A patent/DK160548C/da not_active IP Right Cessation
- 1976-09-22 DE DE2642608A patent/DE2642608C2/de not_active Expired
- 1976-09-22 PT PT65624A patent/PT65624B/pt unknown
- 1976-09-23 AU AU18048/76A patent/AU512445B2/en not_active Ceased
- 1976-09-23 AU AU18048/76A patent/AU1804876A/en not_active Ceased
- 1976-09-24 JP JP51114602A patent/JPS6059228B2/ja not_active Expired
-
1977
- 1977-02-04 FR FR7703256A patent/FR2329665A1/fr active Granted
- 1977-04-22 ES ES458181A patent/ES458181A1/es not_active Expired
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1985
- 1985-06-26 JP JP14012285A patent/JPS6127977A/ja active Granted
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