FI67370C - Mellanprodukt foer framstaellning av 4-(4-disubstituerade piperidinylmetyl)-3,3-difenyl-2-pyrrolidinoner och foerfarande foer framstaellning av mellanprodukten - Google Patents
Mellanprodukt foer framstaellning av 4-(4-disubstituerade piperidinylmetyl)-3,3-difenyl-2-pyrrolidinoner och foerfarande foer framstaellning av mellanprodukten Download PDFInfo
- Publication number
- FI67370C FI67370C FI762694A FI762694A FI67370C FI 67370 C FI67370 C FI 67370C FI 762694 A FI762694 A FI 762694A FI 762694 A FI762694 A FI 762694A FI 67370 C FI67370 C FI 67370C
- Authority
- FI
- Finland
- Prior art keywords
- diphenyl
- pyrrolidinone
- hydroxymethyl
- framstating
- mellan
- Prior art date
Links
- -1 PIPERIDINYLMETHYL Chemical class 0.000 title claims description 18
- 230000004224 protection Effects 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- KTOFYLXSANIPND-UHFFFAOYSA-N 4-(hydroxymethyl)pyrrolidin-2-one Chemical compound OCC1CNC(=O)C1 KTOFYLXSANIPND-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 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 3
- KMDKDQXWHWLFKP-UHFFFAOYSA-N 4-(hydroxymethyl)-3,3-diphenyl-1-propan-2-ylpyrrolidin-2-one Chemical group O=C1N(C(C)C)CC(CO)C1(C=1C=CC=CC=1)C1=CC=CC=C1 KMDKDQXWHWLFKP-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 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 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides 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
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- DILWWMFEHWWBCX-UHFFFAOYSA-N 1-(1-phenylethyl)azetidin-3-ol Chemical compound C=1C=CC=CC=1C(C)N1CC(O)C1 DILWWMFEHWWBCX-UHFFFAOYSA-N 0.000 description 1
- LOUFPHFLZOBIHA-UHFFFAOYSA-N 1-(2-methylpropyl)azetidin-3-ol Chemical compound CC(C)CN1CC(O)C1 LOUFPHFLZOBIHA-UHFFFAOYSA-N 0.000 description 1
- JOXQHYFVXZZGQZ-UHFFFAOYSA-N 1-benzylazetidin-3-ol Chemical compound C1C(O)CN1CC1=CC=CC=C1 JOXQHYFVXZZGQZ-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
- ZBZXLWOOMIFOFF-UHFFFAOYSA-N 1-butylazetidin-3-ol Chemical compound CCCCN1CC(O)C1 ZBZXLWOOMIFOFF-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
- ZMXWVFGREWGXIE-UHFFFAOYSA-N 1-ethylazetidin-3-ol Chemical compound CCN1CC(O)C1 ZMXWVFGREWGXIE-UHFFFAOYSA-N 0.000 description 1
- XSGMJDQRZDWEPW-UHFFFAOYSA-N 1-propan-2-ylazetidin-3-ol Chemical compound CC(C)N1CC(O)C1 XSGMJDQRZDWEPW-UHFFFAOYSA-N 0.000 description 1
- UELHSANKOLQHTB-UHFFFAOYSA-N 1-propylazetidin-3-ol Chemical compound CCCN1CC(O)C1 UELHSANKOLQHTB-UHFFFAOYSA-N 0.000 description 1
- LTXMZCQSCSXXLF-UHFFFAOYSA-N 4-(hydroxymethyl)-1-(2-methylpropyl)-3,3-diphenylpyrrolidin-2-one Chemical compound O=C1N(CC(C)C)CC(CO)C1(C=1C=CC=CC=1)C1=CC=CC=C1 LTXMZCQSCSXXLF-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides 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
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 150000002148 esters Chemical class 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
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration 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
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000002198 insoluble material 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
- 239000010410 layer Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI824104A FI76079C (fi) | 1975-09-23 | 1982-11-29 | 4,5-dihydro-3,3-difenyl-4- hydrokarbylaminometylfuran-2(3h)oner och foerfarande foer deras framstaellning. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61595175 | 1975-09-23 | ||
| US05/615,951 US4119637A (en) | 1975-09-23 | 1975-09-23 | 4-Hydroxymethyl-2-pyrrolidinones |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI762694A7 FI762694A7 (en, 2012) | 1977-03-24 |
| FI67370B FI67370B (fi) | 1984-11-30 |
| FI67370C true FI67370C (fi) | 1985-03-11 |
Family
ID=24467444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI762694A FI67370C (fi) | 1975-09-23 | 1976-09-21 | Mellanprodukt foer framstaellning av 4-(4-disubstituerade piperidinylmetyl)-3,3-difenyl-2-pyrrolidinoner och foerfarande foer framstaellning av mellanprodukten |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4119637A (en, 2012) |
| JP (2) | JPS6059228B2 (en, 2012) |
| AU (2) | AU512445B2 (en, 2012) |
| BE (1) | BE846402A (en, 2012) |
| BR (1) | BR7606209A (en, 2012) |
| CA (1) | CA1077497A (en, 2012) |
| CH (1) | CH616659A5 (en, 2012) |
| DE (2) | DE2661028C2 (en, 2012) |
| DK (1) | DK160548C (en, 2012) |
| ES (2) | ES451752A1 (en, 2012) |
| FI (1) | FI67370C (en, 2012) |
| FR (2) | FR2333792A1 (en, 2012) |
| GB (2) | GB1552687A (en, 2012) |
| IE (1) | IE44843B1 (en, 2012) |
| IL (1) | IL50436A (en, 2012) |
| MX (1) | MX3846E (en, 2012) |
| NL (1) | NL7610526A (en, 2012) |
| PH (1) | PH13940A (en, 2012) |
| PT (1) | PT65624B (en, 2012) |
| SE (1) | SE418397B (en, 2012) |
| ZA (1) | ZA765417B (en, 2012) |
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 (en, 2012) * | 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
-
1985
- 1985-06-26 JP JP14012285A patent/JPS6127977A/ja active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: A.H. ROBINS COMPANY, INCORPORATED |