CH624101A5 - - Google Patents

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Info

Publication number: CH624101A5
Authority: CH; Switzerland
Prior art keywords: methyl; preparation; formula; pyrrolidinone; group
Prior art date: 1976-03-31

Application number

CH400377A

Other languages

English (en)

French (fr)

Inventor

Souli Nanthavong

Charles Pigerol

Pierre Eymard

Jacques Simiand

Original Assignee

Labaz

Priority date (The priority date 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 date listed.)

1976-03-31

Filing date

1977-03-30

Publication date

1981-07-15

1977-03-30 Application filed by Labaz filed Critical Labaz

1981-07-15 Publication of CH624101A5 publication Critical patent/CH624101A5/fr

Links

150000001875 compounds Chemical class 0.000 claims description 79
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 41
238000000034 method Methods 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
238000002360 preparation method Methods 0.000 claims description 38
150000002148 esters Chemical class 0.000 claims description 34
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 claims description 34
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 25
230000008569 process Effects 0.000 claims description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
-1 alkali metal salt Chemical class 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
238000010992 reflux Methods 0.000 claims description 7
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 3
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
230000007717 exclusion Effects 0.000 claims 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
238000005809 transesterification reaction Methods 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 38
239000000203 mixture Substances 0.000 description 32
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 27
238000002329 infrared spectrum Methods 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
125000004494 ethyl ester group Chemical group 0.000 description 21
150000001408 amides Chemical class 0.000 description 18
VTXJIDBQMAXDIY-QKBMRJQYSA-N C[C@H]1CN[C@]2(C[C@H]3O[C@]4(CC(=C)[C@H]5O[C@@](O)([C@H](O)[C@@H]6C[C@H]7O[C@@]8(CC[C@]9(CC=C[C@H](O9)\C=C\CCC(O)=O)O8)[C@H](C)C[C@H]7O6)[C@H](C)[C@H](O)[C@@H]5C)C[C@@H](C)C[C@@H](O4)[C@H]3O2)[C@@H](C)C1 Chemical compound C[C@H]1CN[C@]2(C[C@H]3O[C@]4(CC(=C)[C@H]5O[C@@](O)([C@H](O)[C@@H]6C[C@H]7O[C@@]8(CC[C@]9(CC=C[C@H](O9)\C=C\CCC(O)=O)O8)[C@H](C)C[C@H]7O6)[C@H](C)[C@H](O)[C@@H]5C)C[C@@H](C)C[C@@H](O4)[C@H]3O2)[C@@H](C)C1 VTXJIDBQMAXDIY-QKBMRJQYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
150000003180 prostaglandins Chemical class 0.000 description 14
239000012429 reaction media Substances 0.000 description 14
230000000694 effects Effects 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000012153 distilled water Substances 0.000 description 9
125000000896 monocarboxylic acid group Chemical group 0.000 description 9
230000000144 pharmacologic effect Effects 0.000 description 9
239000000047 product Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
230000009471 action Effects 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
229940126214 compound 3 Drugs 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
229940094443 oxytocics prostaglandins Drugs 0.000 description 6
239000000126 substance Substances 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
229940124630 bronchodilator Drugs 0.000 description 5
229940125782 compound 2 Drugs 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
230000009467 reduction Effects 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
230000003033 spasmogenic effect Effects 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
229940125904 compound 1 Drugs 0.000 description 4
229940125898 compound 5 Drugs 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
230000000968 intestinal effect Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
210000002345 respiratory system Anatomy 0.000 description 4
230000028327 secretion Effects 0.000 description 4
210000002460 smooth muscle Anatomy 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
YTTWDTVYXAEAJA-UHFFFAOYSA-N 2,2-dimethyl-hexanoic acid Chemical compound CCCCC(C)(C)C(O)=O YTTWDTVYXAEAJA-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
208000001953 Hypotension Diseases 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-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
208000005392 Spasm Diseases 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
208000006673 asthma Diseases 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical class CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
239000000499 gel Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
230000001575 pathological effect Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
DWWCZKVBNWJJHC-UHFFFAOYSA-N 6-methoxy-2,3-dihydro-1h-indene-5-carbaldehyde Chemical compound C1=C(C=O)C(OC)=CC2=C1CCC2 DWWCZKVBNWJJHC-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000009079 Bronchial Spasm Diseases 0.000 description 2
208000014181 Bronchial disease Diseases 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
239000000168 bronchodilator agent Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
210000000748 cardiovascular system Anatomy 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000001595 contractor effect Effects 0.000 description 2
230000035487 diastolic blood pressure Effects 0.000 description 2
VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 2
230000008034 disappearance Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
150000002085 enols Chemical class 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
VAJFLSRDMGNZJY-UHFFFAOYSA-N heptylphosphonic acid Chemical compound CCCCCCCP(O)(O)=O VAJFLSRDMGNZJY-UHFFFAOYSA-N 0.000 description 2
208000021822 hypotensive Diseases 0.000 description 2
230000001077 hypotensive effect Effects 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 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
229930014626 natural product Natural products 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
210000000582 semen Anatomy 0.000 description 2
230000004936 stimulating effect Effects 0.000 description 2
230000035488 systolic blood pressure Effects 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
210000004291 uterus Anatomy 0.000 description 2
230000000304 vasodilatating effect Effects 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
LQZCYXCHWNQBKX-UHFFFAOYSA-N 1-dimethoxyphosphorylheptan-2-one Chemical class CCCCCC(=O)CP(=O)(OC)OC LQZCYXCHWNQBKX-UHFFFAOYSA-N 0.000 description 1
YTTWDTVYXAEAJA-UHFFFAOYSA-M 2,2-dimethylhexanoate Chemical compound CCCCC(C)(C)C([O-])=O YTTWDTVYXAEAJA-UHFFFAOYSA-M 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-M 2-ethylhexanoate Chemical compound CCCCC(CC)C([O-])=O OBETXYAYXDNJHR-UHFFFAOYSA-M 0.000 description 1
GHUUIEXEEIVCRY-UHFFFAOYSA-N 3-methoxyoct-1-ene Chemical compound CCCCCC(OC)C=C GHUUIEXEEIVCRY-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
241001494479 Pecora Species 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
208000007888 Sinus Tachycardia Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
JDCLUYDBENDDSR-NSHDSACASA-N [(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-(5-methyl-1,3,4-oxadiazol-2-yl)methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1OC(=NN=1)C JDCLUYDBENDDSR-NSHDSACASA-N 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
230000000026 anti-ulcerogenic effect Effects 0.000 description 1
239000012223 aqueous fraction Substances 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
230000007883 bronchodilation Effects 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000006071 cream Substances 0.000 description 1
229940095074 cyclic amp Drugs 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloro-acetic acid Natural products OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 1
229960005215 dichloroacetic acid Drugs 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000008187 granular material Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
HAPIXNBOBZHNCA-UHFFFAOYSA-N methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Chemical compound COC(=O)C1=CC=C(C)C(B2OC(C)(C)C(C)(C)O2)=C1 HAPIXNBOBZHNCA-UHFFFAOYSA-N 0.000 description 1
210000000754 myometrium Anatomy 0.000 description 1
230000008693 nausea Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
VSMOENVRRABVKN-UHFFFAOYSA-N oct-1-en-3-ol Chemical compound CCCCCC(O)C=C VSMOENVRRABVKN-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000027758 ovulation cycle Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000004040 pyrrolidinones Chemical class 0.000 description 1
230000001603 reducing effect Effects 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 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
238000002560 therapeutic procedure Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000007514 turning Methods 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
230000008673 vomiting Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- 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
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrrole Compounds (AREA)

CH400377A 1976-03-31 1977-03-30 CH624101A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IL49325A IL49325A (en)	1976-03-31	1976-03-31	8-aza-11-deoxy-pge1 derivatives,their preparation and pharmaceutical compositions containing them

Publications (1)

Publication Number	Publication Date
CH624101A5 true CH624101A5 (de)	1981-07-15

Family

ID=11048789

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH400377A CH624101A5 (de)	1976-03-31	1977-03-30
CH697780A CH628032A5 (fr)	1976-03-31	1980-09-17	Procede de preparation de derives de prostaglandine.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH697780A CH628032A5 (fr)	1976-03-31	1980-09-17	Procede de preparation de derives de prostaglandine.

Country Status (18)

Country	Link
US (1)	US4115401A (de)
JP (1)	JPS52142060A (de)
BE (1)	BE852941A (de)
CA (1)	CA1074804A (de)
CH (2)	CH624101A5 (de)
DD (1)	DD130352A5 (de)
DE (1)	DE2714129A1 (de)
ES (1)	ES457385A1 (de)
FR (1)	FR2346332A1 (de)
GB (1)	GB1574246A (de)
HU (1)	HU178040B (de)
IL (1)	IL49325A (de)
IT (1)	IT1075373B (de)
NL (1)	NL7703503A (de)
NO (1)	NO149428C (de)
PL (3)	PL108289B1 (de)
SE (1)	SE417603B (de)
SU (3)	SU676162A3 (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5536475A (en) *	1978-07-11	1980-03-14	Glaxo Group Ltd	Prostanoid compound
US4320136A (en) *	1980-08-11	1982-03-16	E. I. Du Pont De Nemours And Company	8-Aza-16,16-difluoroprostanoids
US4530933A (en) *	1982-12-27	1985-07-23	E. I. Du Pont De Nemours And Company	8-Aza-13-thiaprostanoids and a method of use thereof as anti-ulcer agents
US4456613A (en) *	1982-12-27	1984-06-26	E. I. Du Pont De Nemours And Company	6-Keto- and 6-hydroxy-8-azaprostanoids and anti-ulcer use thereof
PL356662A1 (en)	1999-12-22	2004-06-28	Pfizer Products Inc.	Ep4 receptor selective agonists in the treatment of osteoporosis
NZ525164A (en) *	2000-11-27	2005-04-29	Pfizer Prod Inc	EP4 receptor selective agonists in the treatment of osteoporosis
EP1408961B1 (de) *	2001-07-16	2007-07-11	F. Hoffmann-La Roche Ag	2 pyrrolidon-derivate als prostanoid-agonisten
ES2254726T3 (es)	2001-07-16	2006-06-16	F. Hoffmann-La Roche Ag	Analogos de prostaglandina como agonistas receptores de ep4.
CN101921220B (zh)	2001-07-23	2013-05-22	小野药品工业株式会社	治疗与骨质损失有关的疾病的含有ep4激动剂作为活性成分的药物组合物
EP1481976B1 (de)	2002-03-05	2012-11-07	Ono Pharmaceutical Co., Ltd.	8-azaprostaglandinderivatverbindungen und arzneimittel, die diese verbindungen als wirkstoff enthalten
AU2003209571A1 (en) *	2002-03-18	2003-09-29	Pfizer Products Inc.	Use of selective ep4 receptor agonists for the treatment of liver failure, loss of patency of the ductus arteriosus, glaucoma or ocular hypertension
BRPI0406717A (pt) *	2003-01-10	2005-12-20	Hoffmann La Roche	Composto, composição farmacêutica que compreende o mesmo, método de tratamento de uma enfermidade em um mamìfero, utilização do composto e processo para a sua produção
US7179820B2 (en)	2003-06-06	2007-02-20	Allergan, Inc.	Piperidinyl prostaglandin E analogs
US20080058375A1 (en) *	2004-01-08	2008-03-06	Elworthy Todd R	2-Piperidone derivatives as prostaglandin antagonists

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3975399A (en) *	1974-08-06	1976-08-17	E. I. Du Pont De Nemours And Company	1,5-Disubstituted-2-pyrrolidinones, -3-pyrrolin-2-ones, and -4-pyrrolin-2-ones

1976
- 1976-03-31 IL IL49325A patent/IL49325A/xx unknown
1977
- 1977-03-28 GB GB12991/77A patent/GB1574246A/en not_active Expired
- 1977-03-28 BE BE176164A patent/BE852941A/xx not_active IP Right Cessation
- 1977-03-29 PL PL1977210102A patent/PL108289B1/pl unknown
- 1977-03-29 PL PL1977210101A patent/PL107544B1/pl unknown
- 1977-03-29 PL PL1977197005A patent/PL107643B1/pl unknown
- 1977-03-29 DD DD7700198124A patent/DD130352A5/de unknown
- 1977-03-30 SE SE7703698A patent/SE417603B/xx unknown
- 1977-03-30 NO NO771134A patent/NO149428C/no unknown
- 1977-03-30 CH CH400377A patent/CH624101A5/fr not_active IP Right Cessation
- 1977-03-30 HU HU77LA913A patent/HU178040B/hu unknown
- 1977-03-30 CA CA275,134A patent/CA1074804A/en not_active Expired
- 1977-03-30 DE DE19772714129 patent/DE2714129A1/de not_active Withdrawn
- 1977-03-31 FR FR7709650A patent/FR2346332A1/fr active Granted
- 1977-03-31 ES ES457385A patent/ES457385A1/es not_active Expired
- 1977-03-31 SU SU772465855A patent/SU676162A3/ru active
- 1977-03-31 IT IT21906/77A patent/IT1075373B/it active
- 1977-03-31 NL NL7703503A patent/NL7703503A/xx not_active Application Discontinuation
- 1977-03-31 US US05/783,284 patent/US4115401A/en not_active Expired - Lifetime
- 1977-03-31 JP JP3742877A patent/JPS52142060A/ja active Pending
1978
- 1978-03-30 SU SU782595450A patent/SU715019A3/ru active
- 1978-03-30 SU SU782594353A patent/SU837321A3/ru active
1980
- 1980-09-17 CH CH697780A patent/CH628032A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
IL49325A (en)	1979-11-30
PL107544B1 (pl)	1980-02-29
NL7703503A (nl)	1977-10-04
DE2714129A1 (de)	1977-10-13
GB1574246A (en)	1980-09-03
PL197005A1 (pl)	1978-10-09
SU837321A3 (ru)	1981-06-07
HU178040B (en)	1982-02-28
CA1074804A (en)	1980-04-01
NO149428B (no)	1984-01-09
NO771134L (no)	1977-10-03
US4115401A (en)	1978-09-19
BE852941A (fr)	1977-09-28
SU676162A3 (ru)	1979-07-25
SU715019A3 (ru)	1980-02-05
IT1075373B (it)	1985-04-22
FR2346332A1 (fr)	1977-10-28
CH628032A5 (fr)	1982-02-15
FR2346332B1 (de)	1980-05-09
JPS52142060A (en)	1977-11-26
DD130352A5 (de)	1978-03-22
PL108289B1 (pl)	1980-03-31
PL107643B1 (pl)	1980-02-29
ES457385A1 (es)	1978-02-01
NO149428C (no)	1984-04-18
SE7703698L (sv)	1977-10-01
SE417603B (sv)	1981-03-30
IL49325A0 (en)	1976-05-31

Legal Events

Date	Code	Title	Description
1981-11-13	PFA	Name/firm changed	Owner name: SANOFI
1981-11-13	PUE	Assignment	Owner name: OMNIUM FINANCIER AQUITAINE POUR L'HYGIENE ET LA SA
1985-11-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0253738A1 (de)	1988-01-20	Taxal-Derivate, deren Herstellung und diese enthaltende pharmazeutische Zusammenstellungen
EP0318377A2 (de)	1989-05-31	Enantiomere Derivate von Aminosäure, Verfahren zu deren Herstellung und deren therapeutische Verwendung
FR2517302A1 (fr)	1983-06-03	Esters et amides de 13 14-bisdehydroprostaglandines
CH628032A5 (fr)	1982-02-15	Procede de preparation de derives de prostaglandine.
EP0290321B1 (de)	1991-10-02	Beta-D-Phenyl-Thioxyloside, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
CH632505A5 (fr)	1982-10-15	Nouveaux composes a noyau cyclopropanique, procede de preparation et utilisation a la preparation de derives cyclopropaniques a chaine dihalovinylique.
FR2459248A1 (fr)	1981-01-09	Hemi-esters du cholesterol utilisables en medecine et leur procede de fabrication
EP0729936B1 (de)	1999-07-07	Verfahren zur Synthese der alpha-substiuierten Akrylsäuren und N-(mercaptoacyl)aminsäuren
EP0004493B1 (de)	1981-05-06	Äther deren organische Reste asymmetrische Atome enthalten, Verfahren zu ihrer Herstellung und ihre Anwendung zur Spaltung von Alkoholen, Phenolen oder gewissen Verbindungen mit Laktonstruktur
FR2598420A1 (fr)	1987-11-13	Nouveaux esters retinoiques d'antibiotiques, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
FR2554448A1 (fr)	1985-05-10	Derives furyles de prostaglandines 16-substituees et procede pour leur fabrication
CA1060039A (fr)	1979-08-07	Derives des acides 3-benzoyl-phenylalcanoiques et-alcenoiques
FR2510583A1 (fr)	1983-02-04	Derives nouveaux d'acide ursodesoxycholique, leur procede de preparation et leur application en therapeutique
FR2634766A1 (fr)	1990-02-02	Acides (rs)-2-(2,3-dihydro-5-hydroxy-4,6,7-trimethylbenzofurannyl)-acetiques, et acides 2-(2,3-dihydro-5-acyloxy-4,6,7-trimethylbenzofurannyl)-acetiques et leurs esters, utiles comme medicaments mucoregulateurs et anti-ischemiques, procede pour leur preparation et compositions pharmaceutiques les contenant
CA1094569A (fr)	1981-01-27	Procede de preparation de nouvelles lactones derivees du cyclopentanol
CH644101A5 (fr)	1984-07-13	Analogues de la prostaglandine e(1) et compositions pharmaceutiques les contenant.
EP1230252B1 (de)	2004-04-14	Beta-d-thioxylos-derivate, verfahren zur herstellung und verwendung als arzneimittel
CA1178599A (fr)	1984-11-27	Composes sulfures comportant un cycle lactonique, leur preparation et leur application a la preparation de derives cyclopropaniques
CA1078860A (fr)	1980-06-03	Procedes de synthese de derives de prostaglandines
FR2510577A1 (fr)	1983-02-04	Composes organiques azotes extraits de plantes et leurs derives, leur preparation et leurs utilisations therapeutiques, notamment en tant qu'agents antineoplastiques
CA1090356A (fr)	1980-11-25	Cyclopentanones et leur application dans la synthese des prostaglandines
CH676598A5 (de)	1991-02-15
CH650251A5 (fr)	1985-07-15	Derives d'heteroprostaglandines ainsi que leurs procedes de preparation.
FR2495615A1 (fr)	1982-06-11	Ethers d'hydroxymethylpyrazines substituees, leur preparation et leur utilisation therapeutique en tant qu'agents antilipolytiques, hypotriglyceridemiques et hypocholesterolemiques
CA2031241A1 (fr)	1991-06-02	Intermediaires, leurs procedes de preparation et leur utilisation pour la synthese des vitamines a et e