SE427657B - N-(tetrazol-5-yl)-prostaglandinkarboxamider - Google Patents
N-(tetrazol-5-yl)-prostaglandinkarboxamiderInfo
- Publication number
- SE427657B SE427657B SE7900353A SE7900353A SE427657B SE 427657 B SE427657 B SE 427657B SE 7900353 A SE7900353 A SE 7900353A SE 7900353 A SE7900353 A SE 7900353A SE 427657 B SE427657 B SE 427657B
- Authority
- SE
- Sweden
- Prior art keywords
- alpha
- class
- tetrazol
- trans
- cis
- Prior art date
Links
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 title claims description 33
- 150000003180 prostaglandins Chemical class 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 47
- -1 ethylphenyl Chemical group 0.000 claims description 44
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 230000035558 fertility Effects 0.000 claims description 7
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 230000000767 anti-ulcer Effects 0.000 claims description 4
- 230000004071 biological effect Effects 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 230000003182 bronchodilatating effect Effects 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000243 solution Substances 0.000 description 28
- 239000007858 starting material Substances 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
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- 239000000203 mixture Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
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- 229910002027 silica gel Inorganic materials 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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- 229940124630 bronchodilator Drugs 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 5
- SXXLKZCNJHJYFL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridin-5-ium-3-olate Chemical compound C1CNCC2=C1ONC2=O SXXLKZCNJHJYFL-UHFFFAOYSA-N 0.000 description 4
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 210000000754 myometrium Anatomy 0.000 description 3
- QDMPKKFNRFFSNK-UHFFFAOYSA-N n-(2h-tetrazol-5-yl)formamide Chemical group O=CNC1=NN=NN1 QDMPKKFNRFFSNK-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 239000000376 reactant Substances 0.000 description 3
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
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- 239000008194 pharmaceutical composition Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- DZUXGQBLFALXCR-CDIPTNKSSA-N prostaglandin F1alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O DZUXGQBLFALXCR-CDIPTNKSSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- JJPVWQWOOQYHCB-UHFFFAOYSA-N triethyl(phenyl)azanium Chemical compound CC[N+](CC)(CC)C1=CC=CC=C1 JJPVWQWOOQYHCB-UHFFFAOYSA-N 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86956978A | 1978-01-16 | 1978-01-16 | |
| US89373178A | 1978-04-05 | 1978-04-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7900353L SE7900353L (sv) | 1979-07-17 |
| SE427657B true SE427657B (sv) | 1983-04-25 |
Family
ID=27128123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7900353A SE427657B (sv) | 1978-01-16 | 1979-01-15 | N-(tetrazol-5-yl)-prostaglandinkarboxamider |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS54100378A (de) |
| AR (1) | AR222817A1 (de) |
| AT (1) | AT367755B (de) |
| AU (1) | AU507853B2 (de) |
| CA (1) | CA1152502A (de) |
| CH (1) | CH635833A5 (de) |
| DD (1) | DD141155A5 (de) |
| DE (1) | DE2901476C3 (de) |
| DK (1) | DK523378A (de) |
| ES (1) | ES482421A1 (de) |
| FI (1) | FI790120A (de) |
| FR (1) | FR2414503A1 (de) |
| GB (1) | GB2012272B (de) |
| GR (1) | GR72747B (de) |
| IE (1) | IE48175B1 (de) |
| IL (1) | IL56433A (de) |
| IN (1) | IN150279B (de) |
| IT (1) | IT1110992B (de) |
| LU (1) | LU80789A1 (de) |
| NL (1) | NL7900292A (de) |
| NO (1) | NO790122L (de) |
| NZ (1) | NZ189377A (de) |
| PH (3) | PH15031A (de) |
| PL (1) | PL117869B1 (de) |
| PT (1) | PT69076A (de) |
| SE (1) | SE427657B (de) |
| SU (1) | SU831071A3 (de) |
| YU (1) | YU4579A (de) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE788209A (fr) * | 1971-09-01 | 1973-02-28 | Pfizer | Derives tetrazoyliques des prostaglandines naturelles |
| DD118856A5 (de) * | 1972-11-08 | 1976-03-20 | ||
| IE43462B1 (en) * | 1975-06-23 | 1981-03-11 | Pfizer | Substituted tetranorprostaglandins |
| DE2559093C3 (de) * | 1975-12-30 | 1981-12-24 | Pfizer Inc., 10017 New York, N.Y. | 2-Desarboxy-2-[tetrazol-5-yl]-11-desoxy-ω-pentanorprostaglandine der E- oder F-Reihe und deren C↓15↓-Epimere |
| US4404372A (en) * | 1977-06-13 | 1983-09-13 | Pfizer Inc. | 15-Substituted-ω-pentanorprostaglandin derivatives |
-
1978
- 1978-11-23 DK DK523378A patent/DK523378A/da not_active Application Discontinuation
- 1978-11-23 IN IN841/DEL/78A patent/IN150279B/en unknown
- 1978-12-27 PL PL1978212183A patent/PL117869B1/pl unknown
- 1978-12-27 SU SU782715902A patent/SU831071A3/ru active
- 1978-12-27 DD DD78210198A patent/DD141155A5/de unknown
-
1979
- 1979-01-11 YU YU00045/79A patent/YU4579A/xx unknown
- 1979-01-12 CA CA000319536A patent/CA1152502A/en not_active Expired
- 1979-01-12 JP JP286979A patent/JPS54100378A/ja active Pending
- 1979-01-12 PH PH22056A patent/PH15031A/en unknown
- 1979-01-15 LU LU80789A patent/LU80789A1/fr unknown
- 1979-01-15 PT PT69076A patent/PT69076A/pt unknown
- 1979-01-15 GB GB791428A patent/GB2012272B/en not_active Expired
- 1979-01-15 IT IT19290/79A patent/IT1110992B/it active
- 1979-01-15 NO NO790122A patent/NO790122L/no unknown
- 1979-01-15 NZ NZ189377A patent/NZ189377A/xx unknown
- 1979-01-15 AT AT0027579A patent/AT367755B/de not_active IP Right Cessation
- 1979-01-15 CH CH38079A patent/CH635833A5/fr not_active IP Right Cessation
- 1979-01-15 SE SE7900353A patent/SE427657B/sv not_active IP Right Cessation
- 1979-01-15 IL IL56433A patent/IL56433A/xx unknown
- 1979-01-15 IE IE60/79A patent/IE48175B1/en unknown
- 1979-01-15 AU AU43359/79A patent/AU507853B2/en not_active Ceased
- 1979-01-15 FR FR7900857A patent/FR2414503A1/fr active Granted
- 1979-01-15 GR GR58098A patent/GR72747B/el unknown
- 1979-01-15 NL NL7900292A patent/NL7900292A/xx not_active Application Discontinuation
- 1979-01-15 FI FI790120A patent/FI790120A/fi unknown
- 1979-01-16 DE DE2901476A patent/DE2901476C3/de not_active Expired
- 1979-01-16 AR AR275174A patent/AR222817A1/es active
- 1979-07-11 ES ES482421A patent/ES482421A1/es not_active Expired
- 1979-11-19 PH PH23299A patent/PH15653A/en unknown
- 1979-11-19 PH PH23301A patent/PH15643A/en unknown
Also Published As
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| NUG | Patent has lapsed |
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