DE2453831A1 - Cyclopentanderivate - Google Patents
CyclopentanderivateInfo
- Publication number
- DE2453831A1 DE2453831A1 DE19742453831 DE2453831A DE2453831A1 DE 2453831 A1 DE2453831 A1 DE 2453831A1 DE 19742453831 DE19742453831 DE 19742453831 DE 2453831 A DE2453831 A DE 2453831A DE 2453831 A1 DE2453831 A1 DE 2453831A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- enyl
- carbon atoms
- general formula
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical class C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 76
- -1 3-Hydroxy-3-methyl-5-ethoxypent-1-enyl Chemical group 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 238000002360 preparation method Methods 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclo-pentanone Natural products O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 10
- 231100000252 nontoxic Toxicity 0.000 claims description 10
- 230000003000 nontoxic effect Effects 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 9
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000001940 cyclopentanes Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000004795 grignard reagents Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 238000003747 Grignard reaction Methods 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- YHLSJSCSQGGJGI-UHFFFAOYSA-N methyl 7-[2-(5-ethoxy-3-hydroxy-3-methylpent-1-enyl)-5-oxocyclopentyl]heptanoate Chemical compound CCOCCC(C)(O)C=CC1CCC(=O)C1CCCCCCC(=O)OC YHLSJSCSQGGJGI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- QOAQSBDJYOAGKS-UHFFFAOYSA-N 7-[2-(3-hydroxy-3-methyl-4-propoxybut-1-enyl)-5-oxocyclopentyl]heptanoic acid Chemical compound CCCOCC(C)(O)C=CC1CCC(=O)C1CCCCCCC(O)=O QOAQSBDJYOAGKS-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000007818 Grignard reagent Substances 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- GBLZBXRHZJXGBJ-UHFFFAOYSA-N methyl 7-[2-(3-hydroxy-6-methoxy-3-methylhex-1-enyl)-5-oxocyclopentyl]heptanoate Chemical compound COCCCC(C)(O)C=CC1CCC(=O)C1CCCCCCC(=O)OC GBLZBXRHZJXGBJ-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 122
- 239000000243 solution Substances 0.000 description 66
- 239000000203 mixture Substances 0.000 description 50
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000003960 organic solvent Substances 0.000 description 19
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000000443 aerosol Substances 0.000 description 15
- 239000003380 propellant Substances 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000375 suspending agent Substances 0.000 description 6
- 239000000725 suspension Substances 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 5
- 241001465754 Metazoa Species 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000008247 solid mixture Substances 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- AQYCZAWLMWOKMU-UHFFFAOYSA-N 1-propoxy-3-(triphenyl-$l^{5}-phosphanylidene)propan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)COCCC)C1=CC=CC=C1 AQYCZAWLMWOKMU-UHFFFAOYSA-N 0.000 description 3
- FCBDNJCPZBFBPE-UHFFFAOYSA-N 2-(7-hydroxyheptyl)-3-oxocyclopentane-1-carbonitrile Chemical compound OCCCCCCCC1C(C#N)CCC1=O FCBDNJCPZBFBPE-UHFFFAOYSA-N 0.000 description 3
- LIGQQSVDEWEEPR-UHFFFAOYSA-N 4-[9-(7-hydroxyheptyl)-1,4-dioxaspiro[4.4]nonan-8-yl]-1-propoxybut-3-en-2-one Chemical compound OCCCCCCCC1C(C=CC(=O)COCCC)CCC11OCCO1 LIGQQSVDEWEEPR-UHFFFAOYSA-N 0.000 description 3
- ZVCCZUWDBYVKPG-UHFFFAOYSA-N 5-ethoxy-1-[9-(7-hydroxyheptyl)-1,4-dioxaspiro[4.4]nonan-8-yl]pent-1-en-3-one Chemical compound OCCCCCCCC1C(C=CC(=O)CCOCC)CCC11OCCO1 ZVCCZUWDBYVKPG-UHFFFAOYSA-N 0.000 description 3
- VODBHKJCRNMTGJ-UHFFFAOYSA-N 7-[2-(5-ethoxy-3-hydroxy-3-methylpent-1-enyl)-5-oxocyclopentyl]heptanoic acid Chemical compound CCOCCC(C)(O)C=CC1CCC(=O)C1CCCCCCC(O)=O VODBHKJCRNMTGJ-UHFFFAOYSA-N 0.000 description 3
- XCYJWKOGHKXWJZ-UHFFFAOYSA-N 9-(7-hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-8-carbaldehyde Chemical compound OCCCCCCCC1C(C=O)CCC11OCCO1 XCYJWKOGHKXWJZ-UHFFFAOYSA-N 0.000 description 3
- NMIZDQIYXLCYSI-UHFFFAOYSA-N 9-(7-hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-8-carbonitrile Chemical compound OCCCCCCCC1C(C#N)CCC11OCCO1 NMIZDQIYXLCYSI-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229940117975 chromium trioxide Drugs 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 150000001983 dialkylethers Chemical class 0.000 description 3
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000027119 gastric acid secretion Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 125000003884 phenylalkyl group Chemical group 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 2
- OUIOUYRQXGTWQU-UHFFFAOYSA-N 1-[9-(7-hydroxyheptyl)-1,4-dioxaspiro[4.4]nonan-8-yl]-6-methoxyhex-1-en-3-one Chemical compound OCCCCCCCC1C(C=CC(=O)CCCOC)CCC11OCCO1 OUIOUYRQXGTWQU-UHFFFAOYSA-N 0.000 description 2
- DASDXHZRVCSYEA-UHFFFAOYSA-N 1-chloro-3-propoxypropan-2-one Chemical compound CCCOCC(=O)CCl DASDXHZRVCSYEA-UHFFFAOYSA-N 0.000 description 2
- MZMOPYFNDDILMI-UHFFFAOYSA-N 1-dimethoxyphosphoryl-5-methoxypentan-2-one Chemical compound COCCCC(=O)CP(=O)(OC)OC MZMOPYFNDDILMI-UHFFFAOYSA-N 0.000 description 2
- WDCKVVCOPDJIIB-UHFFFAOYSA-N 2-(7-hydroxyheptyl)cyclopent-2-en-1-one Chemical compound OCCCCCCCC1=CCCC1=O WDCKVVCOPDJIIB-UHFFFAOYSA-N 0.000 description 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
- AMEQIIYEGPCAKB-UHFFFAOYSA-N 7-(oxan-2-yloxy)heptanal Chemical compound O=CCCCCCCOC1CCCCO1 AMEQIIYEGPCAKB-UHFFFAOYSA-N 0.000 description 2
- HVPHTRJYLAXCRG-UHFFFAOYSA-N 7-(oxan-2-yloxy)heptanenitrile Chemical compound N#CCCCCCCOC1CCCCO1 HVPHTRJYLAXCRG-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229940124630 bronchodilator Drugs 0.000 description 2
- 239000000168 bronchodilator agent Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical class O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 description 2
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 230000036543 hypotension Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
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- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical compound OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- 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
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen 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
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen 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 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5269573A GB1448268A (en) | 1973-11-13 | 1973-11-13 | Cyclopentane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2453831A1 true DE2453831A1 (de) | 1975-05-15 |
Family
ID=10464921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742453831 Pending DE2453831A1 (de) | 1973-11-13 | 1974-11-13 | Cyclopentanderivate |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4036872A (enExample) |
| JP (1) | JPS5082038A (enExample) |
| BE (1) | BE822087A (enExample) |
| CA (1) | CA1042881A (enExample) |
| CH (1) | CH596162A5 (enExample) |
| DE (1) | DE2453831A1 (enExample) |
| DK (1) | DK588674A (enExample) |
| FI (1) | FI327774A7 (enExample) |
| FR (1) | FR2250524B1 (enExample) |
| GB (1) | GB1448268A (enExample) |
| HU (1) | HU172494B (enExample) |
| IE (1) | IE41326B1 (enExample) |
| LU (1) | LU71267A1 (enExample) |
| NL (1) | NL7414819A (enExample) |
| SE (1) | SE7414202L (enExample) |
| ZA (1) | ZA747238B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7028833B2 (en) * | 2004-04-09 | 2006-04-18 | Heimbach Gmbh & Co. | Method for connecting the belt ends of transport belts, as well as transport belt and closure aid for carrying out said method |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS503362B1 (enExample) * | 1970-06-10 | 1975-02-04 | ||
| GB1398072A (en) * | 1971-06-14 | 1975-06-18 | May & Baker Ltd | Cyclopentane derivatives |
-
1973
- 1973-11-13 GB GB5269573A patent/GB1448268A/en not_active Expired
-
1974
- 1974-11-11 HU HU74MA00002618A patent/HU172494B/hu unknown
- 1974-11-12 JP JP49129662A patent/JPS5082038A/ja active Pending
- 1974-11-12 CH CH1509674A patent/CH596162A5/xx not_active IP Right Cessation
- 1974-11-12 ZA ZA00747238A patent/ZA747238B/xx unknown
- 1974-11-12 CA CA213,482A patent/CA1042881A/fr not_active Expired
- 1974-11-12 DK DK588674A patent/DK588674A/da unknown
- 1974-11-12 FR FR7437296A patent/FR2250524B1/fr not_active Expired
- 1974-11-12 SE SE7414202A patent/SE7414202L/xx unknown
- 1974-11-12 US US05/523,015 patent/US4036872A/en not_active Expired - Lifetime
- 1974-11-12 BE BE150419A patent/BE822087A/xx unknown
- 1974-11-12 LU LU71267A patent/LU71267A1/xx unknown
- 1974-11-12 IE IE2324/74A patent/IE41326B1/xx unknown
- 1974-11-12 FI FI3277/74A patent/FI327774A7/fi unknown
- 1974-11-13 DE DE19742453831 patent/DE2453831A1/de active Pending
- 1974-11-13 NL NL7414819A patent/NL7414819A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IE41326L (en) | 1975-05-13 |
| BE822087A (fr) | 1975-05-12 |
| GB1448268A (en) | 1976-09-02 |
| FI327774A7 (enExample) | 1975-05-14 |
| CA1042881A (fr) | 1978-11-21 |
| AU7528274A (en) | 1976-05-13 |
| FR2250524A1 (enExample) | 1975-06-06 |
| SE7414202L (enExample) | 1975-05-14 |
| ZA747238B (en) | 1975-11-26 |
| FR2250524B1 (enExample) | 1978-07-28 |
| NL7414819A (nl) | 1975-05-15 |
| LU71267A1 (enExample) | 1975-08-20 |
| HU172494B (hu) | 1978-09-28 |
| JPS5082038A (enExample) | 1975-07-03 |
| IE41326B1 (en) | 1979-12-05 |
| CH596162A5 (enExample) | 1978-02-28 |
| US4036872A (en) | 1977-07-19 |
| DK588674A (enExample) | 1975-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |