JPS6024098B2 - プロスタグランジン類縁体 - Google Patents

プロスタグランジン類縁体

Info

Publication number: JPS6024098B2
Authority: JP; Japan
Prior art keywords: group; hydrogen; methyl; formula; symbol
Prior art date: 1975-01-24
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.): Expired

Application number

JP51006567A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5198249A (xx

Inventor

ウンベルト、グツジ

ロメオ、シアバツチ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Gruppo Lepetit SpA

Original Assignee

Lepetit SpA

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.)

1975-01-24

Filing date

1976-01-23

Publication date

1985-06-11

1976-01-23 Application filed by Lepetit SpA filed Critical Lepetit SpA

1976-08-30 Publication of JPS5198249A publication Critical patent/JPS5198249A/ja

1985-06-11 Publication of JPS6024098B2 publication Critical patent/JPS6024098B2/ja

Status Expired legal-status Critical Current

Links

150000003180 prostaglandins Chemical class 0.000 title claims description 10
239000000203 mixture Substances 0.000 claims description 36
150000001875 compounds Chemical class 0.000 claims description 26
238000000034 method Methods 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
239000000126 substance Substances 0.000 claims description 19
125000004043 oxo group Chemical group O=* 0.000 claims description 16
230000002829 reductive effect Effects 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
239000003153 chemical reaction reagent Substances 0.000 claims description 11
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
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 5
150000002431 hydrogen Chemical group 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
ZKCZXVODRKOWIY-UHFFFAOYSA-N diphenylstannane Chemical compound C=1C=CC=CC=1[SnH2]C1=CC=CC=C1 ZKCZXVODRKOWIY-UHFFFAOYSA-N 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 4
VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 claims 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
239000000047 product Substances 0.000 description 50
238000010521 absorption reaction Methods 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
239000002253 acid Substances 0.000 description 29
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 29
101150041968 CDC13 gene Proteins 0.000 description 28
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
239000003921 oil Substances 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
-1 ammonium cations Chemical class 0.000 description 20
150000002148 esters Chemical class 0.000 description 20
150000004702 methyl esters Chemical class 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 12
239000000243 solution Substances 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000000862 absorption spectrum Methods 0.000 description 9
239000007858 starting material Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
230000000704 physical effect Effects 0.000 description 7
239000002243 precursor Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
238000009833 condensation Methods 0.000 description 6
230000005494 condensation Effects 0.000 description 6
239000000284 extract Substances 0.000 description 6
229910052698 phosphorus Inorganic materials 0.000 description 6
239000011574 phosphorus Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
230000002997 prostaglandinlike Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
125000005907 alkyl ester group Chemical group 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000010828 elution Methods 0.000 description 3
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
101100537937 Caenorhabditis elegans arc-1 gene Proteins 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
230000003182 bronchodilatating effect Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
235000013336 milk Nutrition 0.000 description 2
239000008267 milk Substances 0.000 description 2
210000004080 milk Anatomy 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
125000001424 substituent group Chemical group 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
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 2
MWNGXYTWWGZEQY-UHFFFAOYSA-N (3-methoxy-2-oxoheptyl)phosphonic acid Chemical compound CCCCC(OC)C(=O)CP(O)(O)=O MWNGXYTWWGZEQY-UHFFFAOYSA-N 0.000 description 1
WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
CKGAPNASZQDWOE-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-methoxyheptan-2-one Chemical compound CCCCC(OC)C(=O)CP(=O)(OC)OC CKGAPNASZQDWOE-UHFFFAOYSA-N 0.000 description 1
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
206010000234 Abortion spontaneous Diseases 0.000 description 1
102100022210 COX assembly mitochondrial protein 2 homolog Human genes 0.000 description 1
102100031144 Coilin Human genes 0.000 description 1
241000699800 Cricetinae Species 0.000 description 1
241000219112 Cucumis Species 0.000 description 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
101000900446 Homo sapiens COX assembly mitochondrial protein 2 homolog Proteins 0.000 description 1
241000519695 Ilex integra Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
125000004036 acetal group Chemical group 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
230000001262 anti-secretory effect Effects 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000004531 blood pressure lowering effect Effects 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
101150102523 cdc12 gene Proteins 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
230000008094 contradictory effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
GUBNMFJOJGDCEL-UHFFFAOYSA-N dicyclomine hydrochloride Chemical group [Cl-].C1CCCCC1C1(C(=O)OCC[NH+](CC)CC)CCCCC1 GUBNMFJOJGDCEL-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
210000002011 intestinal secretion Anatomy 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
230000007794 irritation Effects 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
230000003529 luteolytic effect Effects 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
208000015994 miscarriage Diseases 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
108010051876 p80-coilin Proteins 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
235000021395 porridge Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
241000894007 species Species 0.000 description 1
208000000995 spontaneous abortion Diseases 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof

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

JP51006567A 1975-01-24 1976-01-23 プロスタグランジン類縁体 Expired JPS6024098B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB3248/75		1975-01-24
GB3248/75A GB1538871A (en)	1975-01-24	1975-01-24	Prostaglandins

Publications (2)

Publication Number	Publication Date
JPS5198249A JPS5198249A (xx)	1976-08-30
JPS6024098B2 true JPS6024098B2 (ja)	1985-06-11

Family

ID=9754749

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP51006567A Expired JPS6024098B2 (ja)	1975-01-24	1976-01-23	プロスタグランジン類縁体

Country Status (28)

Country	Link
JP (1)	JPS6024098B2 (xx)
AR (1)	AR212328A1 (xx)
AT (1)	AT351186B (xx)
BE (1)	BE837865A (xx)
CA (1)	CA1076569A (xx)
CH (1)	CH609682A5 (xx)
CS (1)	CS187333B2 (xx)
DD (1)	DD122517A5 (xx)
DE (1)	DE2601646A1 (xx)
DK (1)	DK27376A (xx)
FI (1)	FI64578C (xx)
FR (1)	FR2298322A1 (xx)
GB (1)	GB1538871A (xx)
GR (1)	GR58537B (xx)
HU (1)	HU174185B (xx)
IE (1)	IE43821B1 (xx)
IL (1)	IL48870A (xx)
LU (1)	LU74240A1 (xx)
NL (1)	NL185203C (xx)
NO (1)	NO147714C (xx)
NZ (1)	NZ179816A (xx)
PH (1)	PH14040A (xx)
PT (1)	PT64737B (xx)
RO (1)	RO71901A (xx)
SE (1)	SE446726B (xx)
SU (1)	SU607550A3 (xx)
YU (1)	YU40805B (xx)
ZA (1)	ZA7681B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4064350A (en) *	1976-11-22	1977-12-20	G. D. Searle & Co.	15,16-Dihydroxyprostaglandins
US4194055A (en) *	1976-03-03	1980-03-18	American Cyanamid Company	15,16-dioxy prostenoic acids and esters
IT1162731B (it) *	1979-04-10	1987-04-01	Lepetit Spa	16-metil-16-metossi-5,6-diidro-prosta-glandine della serie e1 ad attivita'antisecretoria
JPS56162014A (en) *	1980-05-16	1981-12-12	Nippon Denso Co Ltd	Measuring device for flow rate of gas

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1392716A (en) *	1971-05-11	1975-04-30	Ici Ltd	Moulding
US4304907A (en) *	1972-05-10	1981-12-08	The Upjohn Company	Bicyclo lactone intermediates for prostaglandin analogs

1975
- 1975-01-24 GB GB3248/75A patent/GB1538871A/en not_active Expired
1976
- 1976-01-05 FI FI760002A patent/FI64578C/fi not_active IP Right Cessation
- 1976-01-07 ZA ZA00760081A patent/ZA7681B/xx unknown
- 1976-01-09 GR GR49742A patent/GR58537B/el unknown
- 1976-01-15 YU YU111/76A patent/YU40805B/xx unknown
- 1976-01-16 CS CS76305A patent/CS187333B2/cs unknown
- 1976-01-17 DE DE19762601646 patent/DE2601646A1/de active Granted
- 1976-01-19 IL IL48870A patent/IL48870A/xx unknown
- 1976-01-21 AT AT36776A patent/AT351186B/de not_active IP Right Cessation
- 1976-01-21 RO RO7684563A patent/RO71901A/ro unknown
- 1976-01-22 IE IE120/76A patent/IE43821B1/en unknown
- 1976-01-22 PH PH18006A patent/PH14040A/en unknown
- 1976-01-22 DD DD190915A patent/DD122517A5/xx unknown
- 1976-01-22 FR FR7601707A patent/FR2298322A1/fr active Granted
- 1976-01-23 BE BE163765A patent/BE837865A/xx not_active IP Right Cessation
- 1976-01-23 CH CH83176A patent/CH609682A5/xx not_active IP Right Cessation
- 1976-01-23 PT PT64737A patent/PT64737B/pt unknown
- 1976-01-23 CA CA244,132A patent/CA1076569A/en not_active Expired
- 1976-01-23 NZ NZ179816A patent/NZ179816A/xx unknown
- 1976-01-23 JP JP51006567A patent/JPS6024098B2/ja not_active Expired
- 1976-01-23 SE SE7600729A patent/SE446726B/xx not_active IP Right Cessation
- 1976-01-23 NL NLAANVRAGE7600696,A patent/NL185203C/xx not_active IP Right Cessation
- 1976-01-23 DK DK27376*#A patent/DK27376A/da not_active Application Discontinuation
- 1976-01-23 AR AR262009A patent/AR212328A1/es active
- 1976-01-23 HU HU76LE788A patent/HU174185B/hu not_active IP Right Cessation
- 1976-01-23 SU SU762311606A patent/SU607550A3/ru active
- 1976-01-23 LU LU74240A patent/LU74240A1/xx unknown
- 1976-01-23 NO NO760214A patent/NO147714C/no unknown

Also Published As

Publication number	Publication date
IE43821B1 (en)	1981-06-03
FI64578C (fi)	1983-12-12
GR58537B (en)	1977-10-31
IL48870A0 (en)	1976-03-31
GB1538871A (en)	1979-01-24
PT64737B (fr)	1977-08-12
NO147714B (no)	1983-02-21
PH14040A (en)	1980-12-12
LU74240A1 (xx)	1976-07-23
SU607550A3 (ru)	1978-05-15
NO760214L (xx)	1976-07-27
NL7600696A (nl)	1976-07-27
JPS5198249A (xx)	1976-08-30
AR212328A1 (es)	1978-06-30
CS187333B2 (en)	1979-01-31
FI760002A (xx)	1976-07-25
NL185203C (nl)	1990-02-16
IL48870A (en)	1979-11-30
SE7600729L (sv)	1976-07-25
ZA7681B (en)	1976-12-29
YU11176A (en)	1982-10-31
DK27376A (da)	1976-07-25
BE837865A (fr)	1976-07-23
FI64578B (fi)	1983-08-31
ATA36776A (de)	1978-12-15
DD122517A5 (xx)	1976-10-12
IE43821L (en)	1976-07-24
HU174185B (hu)	1979-11-28
CA1076569A (en)	1980-04-29
AT351186B (de)	1979-07-10
DE2601646C2 (xx)	1987-07-02
FR2298322B1 (xx)	1979-09-21
NO147714C (no)	1983-06-01
YU40805B (en)	1986-06-30
FR2298322A1 (fr)	1976-08-20
DE2601646A1 (de)	1976-07-29
PT64737A (fr)	1976-02-01
CH609682A5 (en)	1979-03-15
SE446726B (sv)	1986-10-06
RO71901A (ro)	1982-02-26
NZ179816A (en)	1978-04-03
NL185203B (nl)	1989-09-18

Publication	Publication Date	Title
DE3153474C2 (xx)	1990-05-31
US4169895A (en)	1979-10-02	Antisecretory 16,16-dimethyl-17-oxaprostaglandins
US4268522A (en)	1981-05-19	13,14-Dihydro-15-alkenyl- and 13,14-dihydro-15-alkynyl prostaglandins and analogs thereof
JPS6024098B2 (ja)	1985-06-11	プロスタグランジン類縁体
US4294849A (en)	1981-10-13	Prostaglandin analogues
US4035415A (en)	1977-07-12	Omega-nor-cycloalkyl-13,14-dehydro-prostaglandins
US4198430A (en)	1980-04-15	13,14-Dehydro-11-deoxy-prostaglandis
DE60024353T2 (de)	2006-08-03	Verfahren zur Herstellung Antiosteoporicagenz
DE68910774T2 (de)	1994-03-24	Cyclopentanheptencarbonsäurederivate und Verfahren zu ihrer Herstellung.
JPS61227544A (ja)	1986-10-09	新規［４．２．０］ビシクロオクタン誘導体
US4074044A (en)	1978-02-14	Cyanoprostaglandins
CA1186305A (en)	1985-04-30	16-methoxy-16-methyl-prostagland in e.sub.1 derivatives, a process for preparing them and their use as gastroprotective agents
US4283417A (en)	1981-08-11	Bronchodialation with 13,14-dihydro-15-alkenyl prostaglandins
JPS6097926A (ja)	1985-05-31	新規な４−ヒドロキシ−２−シクロペンテノン類およびその製造方法
US4632997A (en)	1986-12-30	Method for preparing cis-bicyclo[3.3.0]octylidene derivative
US4220798A (en)	1980-09-02	19-Methyl-9-keto-15-hydroxy-prost-18-enoic acid derivatives and process of their preparation
KR810001216B1 (ko)	1981-09-29	프로스타글란딘계 화합물의 제조방법
US3998852A (en)	1976-12-21	Novel prostaglandin intermediates and process for the production thereof
US4169145A (en)	1979-09-25	ω-Nor-cycloalkyl-13,14-dehydro-prostaglandins
CA1183839A (en)	1985-03-12	Bicyclic prostaglandins and process for their preparation
AT372080B (de)	1983-08-25	Verfahren zum herstellen von neuen optisch aktiven prost-5-en-13-in-carbonsaeurederivaten
CA1186306A (en)	1985-04-30	Optically active 16-methoxy-16-methyl-prostaglandin e derivatives and a process for preparing them
US4309351A (en)	1982-01-05	Chemical synthesis
JPS60166644A (ja)	1985-08-29	シス−ビシクロ〔３．３．０〕オクチリデン誘導体の製造方法
JPH0651676B2 (ja)	1994-07-06	（５ｅ）−プロスタグランジンｅ▲下２▼類の製造法