CH626325A5 - - Google Patents
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- CH626325A5 CH626325A5 CH1549975A CH1549975A CH626325A5 CH 626325 A5 CH626325 A5 CH 626325A5 CH 1549975 A CH1549975 A CH 1549975A CH 1549975 A CH1549975 A CH 1549975A CH 626325 A5 CH626325 A5 CH 626325A5
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- CH
- Switzerland
- Prior art keywords
- formula
- radical
- compound
- compounds
- ester
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- 150000001875 compounds Chemical class 0.000 claims description 103
- 238000000034 method Methods 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 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 description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 229940014800 succinic anhydride Drugs 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 59
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- -1 aliphatic radicals Chemical class 0.000 description 32
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 230000000694 effects Effects 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 241000700159 Rattus Species 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 210000004051 gastric juice Anatomy 0.000 description 10
- 230000028327 secretion Effects 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 230000000144 pharmacologic effect Effects 0.000 description 9
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- DOQJUNNMZNNQAD-UHFFFAOYSA-N pyrrolidine-2,4-dione Chemical compound O=C1CNC(=O)C1 DOQJUNNMZNNQAD-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 7
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 7
- 150000003180 prostaglandins Chemical class 0.000 description 7
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 6
- ICZVBOAABXHPSZ-UHFFFAOYSA-N piperidine-2,5-dione Chemical compound O=C1CCC(=O)NC1 ICZVBOAABXHPSZ-UHFFFAOYSA-N 0.000 description 6
- 230000002997 prostaglandinlike Effects 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 229940124630 bronchodilator Drugs 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229940126601 medicinal product Drugs 0.000 description 5
- 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 5
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 102000008186 Collagen Human genes 0.000 description 4
- 108010035532 Collagen Proteins 0.000 description 4
- 230000003509 anti-fertility effect Effects 0.000 description 4
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- 230000004872 arterial blood pressure Effects 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 229920001436 collagen Polymers 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 210000002345 respiratory system Anatomy 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- PEATYEGLPLYRIN-UHFFFAOYSA-N 2-aminononanedioic acid Chemical compound OC(=O)C(N)CCCCCCC(O)=O PEATYEGLPLYRIN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000699694 Gerbillinae Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000001072 colon Anatomy 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 3
- 230000001631 hypertensive effect Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- 230000036581 peripheral resistance Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 210000002460 smooth muscle Anatomy 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 2
- LOLKAJARZKDJTD-UHFFFAOYSA-N 4-Ethoxy-4-oxobutanoic acid Chemical compound CCOC(=O)CCC(O)=O LOLKAJARZKDJTD-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 108010079943 Pentagastrin Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000000168 bronchodilator agent 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
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 230000005792 cardiovascular activity Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- YHIMFWJZBVHIPZ-UHFFFAOYSA-N diethyl 2-aminononanedioate Chemical compound CCOC(=O)CCCCCCC(N)C(=O)OCC YHIMFWJZBVHIPZ-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 210000001105 femoral artery Anatomy 0.000 description 2
- 230000035558 fertility Effects 0.000 description 2
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- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229960002449 glycine Drugs 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- UPZGJLYTRBYTLM-UHFFFAOYSA-M lithium;iodide;dihydrate Chemical compound [Li+].O.O.[I-] UPZGJLYTRBYTLM-UHFFFAOYSA-M 0.000 description 2
- 210000003141 lower extremity Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 2
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- PTBUUZMYOHEHAJ-UHFFFAOYSA-N 3-phenylmethoxynonan-1-amine Chemical compound CCCCCCC(CCN)OCC1=CC=CC=C1 PTBUUZMYOHEHAJ-UHFFFAOYSA-N 0.000 description 1
- BDJWIZCZBIOLON-UHFFFAOYSA-N 6-heptyl-1-octylpiperidine-2,5-dione Chemical compound CCCCCCCCN1C(CCCCCCC)C(=O)CCC1=O BDJWIZCZBIOLON-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010003497 Asphyxia Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
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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
- 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
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two 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
- C07D207/36—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51733/74A GB1524818A (en) | 1974-11-29 | 1974-11-29 | 12-azaprostaglandins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626325A5 true CH626325A5 (ko) | 1981-11-13 |
Family
ID=10461163
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1549975A CH626325A5 (ko) | 1974-11-29 | 1975-11-28 | |
| CH209180A CH629748A5 (de) | 1974-11-29 | 1980-03-17 | Verfahren zur herstellung von neuen substituierten aminosaeuren oder von deren estern oder amiden. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209180A CH629748A5 (de) | 1974-11-29 | 1980-03-17 | Verfahren zur herstellung von neuen substituierten aminosaeuren oder von deren estern oder amiden. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4299970A (ko) |
| JP (1) | JPS51125278A (ko) |
| AT (1) | AT359216B (ko) |
| AU (2) | AU496753B2 (ko) |
| BE (1) | BE835989A (ko) |
| CA (1) | CA1088062A (ko) |
| CH (2) | CH626325A5 (ko) |
| DE (1) | DE2552312A1 (ko) |
| DK (1) | DK539775A (ko) |
| ES (1) | ES443081A1 (ko) |
| FI (1) | FI753341A (ko) |
| FR (2) | FR2313043A1 (ko) |
| GB (1) | GB1524818A (ko) |
| HU (2) | HU176752B (ko) |
| IE (1) | IE41877B1 (ko) |
| NL (1) | NL7513903A (ko) |
| NO (2) | NO753935L (ko) |
| SE (2) | SE413505B (ko) |
| ZA (1) | ZA757121B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2362839A1 (fr) * | 1976-06-03 | 1978-03-24 | Wellcome Found | Derives de l'hydantoine et medicaments contenant ces substances |
| IL53559A0 (en) | 1976-12-18 | 1978-03-10 | Beecham Group Ltd | Novel prostaglandin analogues their preparation and pharmaceutical compositions containing them |
| EP0007180B1 (en) * | 1978-06-15 | 1983-03-30 | Beecham Group Plc | Prostaglandin analogue triazole derivatives, processes for their preparation and a pharmaceutical composition containing them |
| AU4806879A (en) * | 1978-06-15 | 1979-12-20 | Beecham Group Limited | 1,2,4 triazole derivatives |
| IL58384A0 (en) * | 1978-10-14 | 1980-01-31 | Beecham Group Ltd | 12-aza analogues of prostcyclin their preparation and pharmaceutical composition containing them |
| US6211226B1 (en) * | 1998-12-17 | 2001-04-03 | Alcon Laboratories, Inc. | 11-Aza prostaglandins for the treatment of glaucoma and ocular hypertension |
| WO2003103604A2 (en) * | 2002-06-01 | 2003-12-18 | Applied Research Systems Ars Holding N.V | Gamma lactams as prostaglandin agonists and use thereof |
| US7053085B2 (en) * | 2003-03-26 | 2006-05-30 | Merck & Co. Inc. | EP4 receptor agonist, compositions and methods thereof |
| US7179820B2 (en) * | 2003-06-06 | 2007-02-20 | Allergan, Inc. | Piperidinyl prostaglandin E analogs |
| US6747037B1 (en) * | 2003-06-06 | 2004-06-08 | Allergan, Inc. | Piperidinyl prostaglandin E analogs |
| US7696243B2 (en) * | 2004-12-06 | 2010-04-13 | Merck Serono, S.A. | Pyrrolidin-2-one derivatives for use as DP1 receptor agonists |
| WO2023212495A1 (en) * | 2022-04-29 | 2023-11-02 | Zymergen Inc. | Novel bio-based compound, method of forming the compound, and adhesive compositions containing the novel compound |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2343769A (en) * | 1941-09-27 | 1944-03-07 | Du Pont | Aliphatic aminoacyl compound and method for preparing same |
| US2582257A (en) * | 1950-09-15 | 1952-01-15 | Parke Davis & Co | Esters and methods for obtaining the same |
| NZ182263A (en) * | 1975-10-25 | 1979-01-11 | Beecham Group Ltd | 2-carboxyalkyl-4,4-dimethyl-1-hydroxy-alkyl-pyrrolidin-3,5-dione derivativesand pharmaceutical compositions |
| NZ182264A (en) * | 1975-10-25 | 1979-01-11 | Beecham Group Ltd | 2-carboxyalkyl-1-hydroxyalkyl-pyrrolidin-3,5-dione or-piperidin-3,6-dione derivatives prarmaceutical compostions |
| US4201864A (en) * | 1975-10-25 | 1980-05-06 | Beecham Group Limited | Oxy-alkylamino acids and esters |
-
1974
- 1974-11-29 GB GB51733/74A patent/GB1524818A/en not_active Expired
-
1975
- 1975-11-07 IE IE2433/75A patent/IE41877B1/en unknown
- 1975-11-12 ZA ZA00757121A patent/ZA757121B/xx unknown
- 1975-11-21 NO NO753935A patent/NO753935L/no unknown
- 1975-11-21 DE DE19752552312 patent/DE2552312A1/de not_active Withdrawn
- 1975-11-25 SE SE7513255A patent/SE413505B/xx unknown
- 1975-11-26 AT AT898375A patent/AT359216B/de not_active IP Right Cessation
- 1975-11-26 FR FR7536139A patent/FR2313043A1/fr active Granted
- 1975-11-26 BE BE162217A patent/BE835989A/xx unknown
- 1975-11-26 FI FI753341A patent/FI753341A/fi not_active Application Discontinuation
- 1975-11-28 CH CH1549975A patent/CH626325A5/de not_active IP Right Cessation
- 1975-11-28 HU HU75BE1328A patent/HU176752B/hu unknown
- 1975-11-28 CA CA240,725A patent/CA1088062A/en not_active Expired
- 1975-11-28 NL NL7513903A patent/NL7513903A/xx not_active Application Discontinuation
- 1975-11-28 DK DK539775A patent/DK539775A/da not_active Application Discontinuation
- 1975-11-28 HU HU75BE1244A patent/HU174537B/hu unknown
- 1975-11-28 AU AU87107/75A patent/AU496753B2/en not_active Expired
- 1975-11-28 JP JP50142811A patent/JPS51125278A/ja active Pending
- 1975-11-29 ES ES443081A patent/ES443081A1/es not_active Expired
-
1978
- 1978-04-07 FR FR7810380A patent/FR2379510A1/fr active Granted
- 1978-08-30 AU AU39427/78A patent/AU526356B2/en not_active Expired
- 1978-09-20 SE SE7809907A patent/SE7809907L/xx unknown
- 1978-11-09 NO NO783765A patent/NO783765L/no unknown
-
1980
- 1980-03-17 CH CH209180A patent/CH629748A5/de not_active IP Right Cessation
- 1980-08-25 US US06/181,432 patent/US4299970A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1524818A (en) | 1978-09-13 |
| FR2379510A1 (fr) | 1978-09-01 |
| SE413505B (sv) | 1980-06-02 |
| DK539775A (da) | 1976-05-30 |
| ATA898375A (de) | 1980-03-15 |
| AU8710775A (en) | 1977-06-02 |
| HU174537B (hu) | 1980-02-28 |
| AU3942778A (en) | 1980-03-06 |
| ZA757121B (en) | 1976-10-27 |
| SE7513255L (sv) | 1976-05-31 |
| HU176752B (en) | 1981-05-28 |
| US4299970A (en) | 1981-11-10 |
| IE41877L (en) | 1976-05-29 |
| ES443081A1 (es) | 1977-05-01 |
| IE41877B1 (en) | 1980-04-09 |
| JPS51125278A (en) | 1976-11-01 |
| FI753341A (ko) | 1976-05-30 |
| CA1088062A (en) | 1980-10-21 |
| NO753935L (ko) | 1976-06-01 |
| FR2313043A1 (fr) | 1976-12-31 |
| BE835989A (fr) | 1976-05-26 |
| FR2379510B1 (ko) | 1982-10-29 |
| AU496753B2 (en) | 1978-10-26 |
| NO783765L (no) | 1976-06-01 |
| FR2313043B1 (ko) | 1982-08-13 |
| NL7513903A (nl) | 1976-06-01 |
| AT359216B (de) | 1980-10-27 |
| SE7809907L (sv) | 1978-09-20 |
| CH629748A5 (de) | 1982-05-14 |
| AU526356B2 (en) | 1983-01-06 |
| DE2552312A1 (de) | 1976-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |