FI65429C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara heterocykliska derivat av (4-fenyl-piperazin-1-yl-aryloximetyl-1,3-dioxolan-2-yl)-metyl-1h-imidazoler och 1h-1,2,4-triazoler - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara heterocykliska derivat av (4-fenyl-piperazin-1-yl-aryloximetyl-1,3-dioxolan-2-yl)-metyl-1h-imidazoler och 1h-1,2,4-triazoler Download PDFInfo
- Publication number
- FI65429C FI65429C FI791989A FI791989A FI65429C FI 65429 C FI65429 C FI 65429C FI 791989 A FI791989 A FI 791989A FI 791989 A FI791989 A FI 791989A FI 65429 C FI65429 C FI 65429C
- Authority
- FI
- Finland
- Prior art keywords
- phenyl
- formula
- triazol
- ylmethyl
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 230000001225 therapeutic effect Effects 0.000 title description 3
- -1 alkali metal azide Chemical class 0.000 claims description 83
- 150000001875 compounds Chemical class 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 31
- 238000003756 stirring Methods 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000007126 N-alkylation reaction Methods 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical class [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 claims description 2
- NFTCRBYUVWQPPQ-UHFFFAOYSA-N 4-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]-2,5-dimethyl-1,2,4-triazol-3-one Chemical compound CC1=NN(C)C(=O)N1C1=CC=C(N2CCN(CC2)C=2C=CC(O)=CC=2)C=C1 NFTCRBYUVWQPPQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
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- PEUPUKDBCPLDIH-UHFFFAOYSA-N 1,2,4-triazole Chemical group C1=NC=N[N]1 PEUPUKDBCPLDIH-UHFFFAOYSA-N 0.000 claims 1
- KWQNDZUBCKHTKU-UHFFFAOYSA-N 1,3-dioxolan-4-ylmethyl methanesulfonate Chemical compound CS(=O)(=O)OCC1COCO1 KWQNDZUBCKHTKU-UHFFFAOYSA-N 0.000 claims 1
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- 239000003054 catalyst Substances 0.000 description 11
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 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
- 229940024986 topical antifungal imidazole and triazole derivative Drugs 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91933378A | 1978-06-23 | 1978-06-23 | |
| US91933378 | 1978-06-23 | ||
| US2038379 | 1979-03-14 | ||
| US06/020,383 US4267179A (en) | 1978-06-23 | 1979-03-14 | Heterocyclic derivatives of (4-phenylpiperazin-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI791989A7 FI791989A7 (fi) | 1979-12-24 |
| FI65429B FI65429B (fi) | 1984-01-31 |
| FI65429C true FI65429C (fi) | 1984-05-10 |
Family
ID=26693375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI791989A FI65429C (fi) | 1978-06-23 | 1979-06-21 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara heterocykliska derivat av (4-fenyl-piperazin-1-yl-aryloximetyl-1,3-dioxolan-2-yl)-metyl-1h-imidazoler och 1h-1,2,4-triazoler |
Country Status (19)
| Country | Link |
|---|---|
| AT (1) | ATE5140T1 (ro) |
| BG (2) | BG50387A3 (ro) |
| DE (1) | DE2966346D1 (ro) |
| DK (1) | DK160428C (ro) |
| ES (1) | ES481771A1 (ro) |
| FI (1) | FI65429C (ro) |
| GR (1) | GR64910B (ro) |
| HK (1) | HK74984A (ro) |
| HU (1) | HU187744B (ro) |
| IE (1) | IE48762B1 (ro) |
| IL (1) | IL57625A (ro) |
| MA (1) | MA18488A1 (ro) |
| NO (1) | NO153297C (ro) |
| NZ (1) | NZ190746A (ro) |
| PH (1) | PH16198A (ro) |
| PT (1) | PT69805A (ro) |
| RO (1) | RO77325A (ro) |
| SG (1) | SG45184G (ro) |
| YU (1) | YU42188B (ro) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3404819A1 (de) * | 1984-02-10 | 1985-08-14 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Neue 1,3-dioxolanylderivate, verfahren zu ihrer herstellung, ihre verwendung und diese verbindungen enthaltendes arzneimittel |
-
1979
- 1979-06-02 GR GR59256A patent/GR64910B/el unknown
- 1979-06-08 PH PH22632A patent/PH16198A/en unknown
- 1979-06-13 DE DE7979301129T patent/DE2966346D1/de not_active Expired
- 1979-06-13 AT AT79301129T patent/ATE5140T1/de active
- 1979-06-15 NZ NZ190746A patent/NZ190746A/xx unknown
- 1979-06-19 HU HU79JA849A patent/HU187744B/hu unknown
- 1979-06-21 DK DK261479A patent/DK160428C/da not_active IP Right Cessation
- 1979-06-21 ES ES481771A patent/ES481771A1/es not_active Expired
- 1979-06-21 FI FI791989A patent/FI65429C/fi not_active IP Right Cessation
- 1979-06-22 MA MA18683A patent/MA18488A1/fr unknown
- 1979-06-22 NO NO792111A patent/NO153297C/no unknown
- 1979-06-22 PT PT69805A patent/PT69805A/pt active IP Right Revival
- 1979-06-22 YU YU1478/79A patent/YU42188B/xx unknown
- 1979-06-22 IL IL57625A patent/IL57625A/xx unknown
- 1979-06-22 BG BG044030A patent/BG50387A3/xx unknown
- 1979-06-23 RO RO7997935A patent/RO77325A/ro unknown
- 1979-08-08 IE IE1178/79A patent/IE48762B1/en active Protection Beyond IP Right Term
-
1984
- 1984-06-19 SG SG45184A patent/SG45184G/en unknown
- 1984-10-04 HK HK749/84A patent/HK74984A/en not_active IP Right Cessation
-
1993
- 1993-06-16 BG BG097871A patent/BG60430B2/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE5140T1 (de) | 1983-11-15 |
| YU42188B (en) | 1988-06-30 |
| SG45184G (en) | 1985-03-08 |
| PH16198A (en) | 1983-07-28 |
| NO153297B (no) | 1985-11-11 |
| MA18488A1 (fr) | 1979-12-31 |
| IE791178L (en) | 1979-12-23 |
| GR64910B (en) | 1980-06-09 |
| PT69805A (en) | 1979-07-01 |
| NO792111L (no) | 1979-12-28 |
| DE2966346D1 (en) | 1983-12-01 |
| DK261479A (da) | 1979-12-24 |
| IL57625A0 (en) | 1979-10-31 |
| FI65429B (fi) | 1984-01-31 |
| ES481771A1 (es) | 1980-07-01 |
| RO77325A (ro) | 1981-08-17 |
| BG60430B2 (bg) | 1995-03-31 |
| NZ190746A (en) | 1981-12-15 |
| NO153297C (no) | 1986-02-19 |
| DK160428B (da) | 1991-03-11 |
| HU187744B (en) | 1986-02-28 |
| YU147879A (en) | 1983-12-31 |
| DK160428C (da) | 1991-08-19 |
| IL57625A (en) | 1983-12-30 |
| BG50387A3 (en) | 1992-07-15 |
| IE48762B1 (en) | 1985-05-15 |
| FI791989A7 (fi) | 1979-12-24 |
| HK74984A (en) | 1984-10-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired | ||
| ND | Supplementary protection certificate (spc) granted | ||
| SPCG | Supplementary protection certificate granted |
Spc suppl protection certif: L33 Extension date: 20031215 |
|
| MA | Patent expired |
Owner name: JANSSEN PHARMACEUTICA N.V. |