FI68615C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 15sulfonamidprostaglandinderivat - Google Patents

Foerfarande foer framstaellning av terapeutiskt anvaendbara 15sulfonamidprostaglandinderivat Download PDF

Info

Publication number: FI68615C
Authority: FI; Finland
Prior art keywords: solution; acid; reaction; lactone; mmol
Prior art date: 1979-09-17

Application number

FI802904A

Other languages

English (en)

Finnish (fi)

Other versions

FI68615B (fi

FI802904A (fi

Inventor

Thomas Ken Schaaf

James Frederick Eggler

Original Assignee

Pfizer

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.)

1979-09-17

Filing date

1980-09-16

Publication date

1985-10-10

1980-09-16 Application filed by Pfizer filed Critical Pfizer

1981-03-18 Publication of FI802904A publication Critical patent/FI802904A/fi

1985-06-28 Publication of FI68615B publication Critical patent/FI68615B/fi

1985-10-10 Application granted granted Critical

1985-10-10 Publication of FI68615C publication Critical patent/FI68615C/fi

Links

-1 tetrahydropyranyloxy Chemical group 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
229940124530 sulfonamide Drugs 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
238000000034 method Methods 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
SXXLKZCNJHJYFL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridin-5-ium-3-olate Chemical compound C1CNCC2=C1ONC2=O SXXLKZCNJHJYFL-UHFFFAOYSA-N 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
101000799461 Homo sapiens Thrombopoietin Proteins 0.000 claims description 3
102100034195 Thrombopoietin Human genes 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
101150116986 THPO gene Proteins 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 21
239000000047 product Substances 0.000 description 17
238000000746 purification Methods 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
230000000694 effects Effects 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
238000007796 conventional method Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
150000003180 prostaglandins Chemical class 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
230000008878 coupling Effects 0.000 description 9
238000010168 coupling process Methods 0.000 description 9
238000005859 coupling reaction Methods 0.000 description 9
150000002576 ketones Chemical class 0.000 description 9
QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical compound N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
239000012267 brine Substances 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
238000012360 testing method Methods 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
125000003180 beta-lactone group Chemical group 0.000 description 7
150000002596 lactones Chemical class 0.000 description 7
229940094443 oxytocics prostaglandins Drugs 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000002373 hemiacetals Chemical group 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
241000282472 Canis lupus familiaris Species 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 5
229960002986 dinoprostone Drugs 0.000 description 5
239000003480 eluent Substances 0.000 description 5
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
241000700199 Cavia porcellus Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000003810 Jones reagent Substances 0.000 description 4
239000012530 fluid Substances 0.000 description 4
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
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230000029058 respiratory gaseous exchange Effects 0.000 description 4
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238000004809 thin layer chromatography Methods 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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239000003054 catalyst Substances 0.000 description 3
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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 3
229960000444 pentagastrin Drugs 0.000 description 3
230000001766 physiological effect Effects 0.000 description 3
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 3
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230000004044 response Effects 0.000 description 3
210000002460 smooth muscle Anatomy 0.000 description 3
239000001476 sodium potassium tartrate Substances 0.000 description 3
235000011006 sodium potassium tartrate Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
206010012735 Diarrhoea Diseases 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
241001274216 Naso Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
230000007883 bronchodilation Effects 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
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238000002347 injection Methods 0.000 description 2
229910003002 lithium salt Inorganic materials 0.000 description 2
159000000002 lithium salts Chemical class 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
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
NQTSTBMCCAVWOS-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-phenoxypropan-2-one Chemical compound COP(=O)(OC)CC(=O)COC1=CC=CC=C1 NQTSTBMCCAVWOS-UHFFFAOYSA-N 0.000 description 1
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
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206010006482 Bronchospasm Diseases 0.000 description 1
241000282465 Canis Species 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
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239000004264 Petrolatum Substances 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
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208000003443 Unconsciousness Diseases 0.000 description 1
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238000007239 Wittig reaction Methods 0.000 description 1
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239000007900 aqueous suspension Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
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235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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238000004587 chromatography analysis Methods 0.000 description 1
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238000010586 diagram Methods 0.000 description 1
KPVWDKBJLIDKEP-UHFFFAOYSA-L dihydroxy(dioxo)chromium;sulfuric acid Chemical compound OS(O)(=O)=O.O[Cr](O)(=O)=O KPVWDKBJLIDKEP-UHFFFAOYSA-L 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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238000002474 experimental method Methods 0.000 description 1
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235000013305 food Nutrition 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
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235000011852 gelatine desserts Nutrition 0.000 description 1
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229960004931 histamine dihydrochloride Drugs 0.000 description 1
PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
238000009802 hysterectomy Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
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230000002401 inhibitory effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
125000000686 lactone group Chemical group 0.000 description 1
150000002597 lactoses Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
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CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
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235000012141 vanillin Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
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239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- 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
- C07D309/04—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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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)

FI802904A 1979-09-17 1980-09-16 Foerfarande foer framstaellning av terapeutiskt anvaendbara 15sulfonamidprostaglandinderivat FI68615C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7652079		1979-09-17
US06/076,520 US4232173A (en)	1979-09-17	1979-09-17	15-Sulfonamidoprostaglandin derivatives

Publications (3)

Publication Number	Publication Date
FI802904A FI802904A (fi)	1981-03-18
FI68615B FI68615B (fi)	1985-06-28
FI68615C true FI68615C (fi)	1985-10-10

Family

ID=22132532

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI802904A FI68615C (fi)	1979-09-17	1980-09-16	Foerfarande foer framstaellning av terapeutiskt anvaendbara 15sulfonamidprostaglandinderivat

Country Status (18)

Country	Link
US (1)	US4232173A (es)
EP (1)	EP0025687B1 (es)
JP (1)	JPS5951938B2 (es)
KR (1)	KR840000964B1 (es)
AR (1)	AR225776A1 (es)
AT (1)	ATE1858T1 (es)
AU (1)	AU518068B2 (es)
CA (1)	CA1153368A (es)
DE (1)	DE3061160D1 (es)
DK (1)	DK392580A (es)
ES (1)	ES8106489A1 (es)
FI (1)	FI68615C (es)
GR (1)	GR70288B (es)
IE (1)	IE50266B1 (es)
IL (1)	IL61038A (es)
PH (1)	PH15098A (es)
PT (1)	PT71807B (es)
YU (1)	YU236180A (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61126069A (ja) *	1984-11-21	1986-06-13	Res Dev Corp Of Japan	プロスタグランジン誘導体
JPS63207015A (ja) *	1987-02-23	1988-08-26	株式会社日立製作所	遮断器装置
JPS6429564A (en) *	1987-07-25	1989-01-31	Oyo Kikaku Kk	Common joist mechanism
US5387608A (en) *	1993-08-17	1995-02-07	Allergan, Inc.	Cyclopentane(ene) heptanoic or cyclopentane(ene) heptenoic acid, 2-hydrocarbyl sulfonamidomethyl and derivatives thereof as therapeutic agents
US5607415A (en) *	1994-08-18	1997-03-04	Kimberly-Clark Corporation	Flexible absorbent article

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3835179A (en) *	1972-07-24	1974-09-10	American Cyanamid Co	Novel 15-substituted prostanoic acids and esters
US4033996A (en) *	1973-04-25	1977-07-05	Merck & Co., Inc.	8-Aza-9-oxo(and dioxo)-thia-11,12-secoprostaglandins
GB1507211A (en) *	1975-02-14	1978-04-12	Ono Pharmaceutical Co	Prostaglandin analogues

1979
- 1979-09-17 US US06/076,520 patent/US4232173A/en not_active Expired - Lifetime
1980
- 1980-09-09 DE DE8080303155T patent/DE3061160D1/de not_active Expired
- 1980-09-09 AT AT80303155T patent/ATE1858T1/de not_active IP Right Cessation
- 1980-09-09 EP EP80303155A patent/EP0025687B1/en not_active Expired
- 1980-09-15 PT PT71807A patent/PT71807B/pt unknown
- 1980-09-15 GR GR62889A patent/GR70288B/el unknown
- 1980-09-15 CA CA000360249A patent/CA1153368A/en not_active Expired
- 1980-09-15 IL IL61038A patent/IL61038A/xx unknown
- 1980-09-15 YU YU02361/80A patent/YU236180A/xx unknown
- 1980-09-15 IE IE1927/80A patent/IE50266B1/en unknown
- 1980-09-16 AU AU62436/80A patent/AU518068B2/en not_active Ceased
- 1980-09-16 ES ES495101A patent/ES8106489A1/es not_active Expired
- 1980-09-16 PH PH24591A patent/PH15098A/en unknown
- 1980-09-16 JP JP55128465A patent/JPS5951938B2/ja not_active Expired
- 1980-09-16 FI FI802904A patent/FI68615C/fi not_active IP Right Cessation
- 1980-09-16 DK DK392580A patent/DK392580A/da not_active Application Discontinuation
- 1980-09-16 KR KR1019800003623A patent/KR840000964B1/ko active
- 1980-09-17 AR AR282561A patent/AR225776A1/es active

Also Published As

Publication number	Publication date
EP0025687B1 (en)	1982-11-24
PT71807B (en)	1981-07-02
IE801927L (en)	1981-03-17
KR840000964B1 (ko)	1984-07-02
FI68615B (fi)	1985-06-28
IE50266B1 (en)	1986-03-19
PH15098A (en)	1982-08-10
JPS5651448A (en)	1981-05-09
IL61038A (en)	1983-12-30
DE3061160D1 (en)	1982-12-30
KR830003415A (ko)	1983-06-20
AU6243680A (en)	1981-03-26
GR70288B (es)	1982-09-03
PT71807A (en)	1980-10-01
FI802904A (fi)	1981-03-18
ATE1858T1 (de)	1982-12-15
EP0025687A1 (en)	1981-03-25
US4232173A (en)	1980-11-04
DK392580A (da)	1981-03-18
IL61038A0 (en)	1980-11-30
CA1153368A (en)	1983-09-06
JPS5951938B2 (ja)	1984-12-17
ES495101A0 (es)	1981-08-16
AR225776A1 (es)	1982-04-30
ES8106489A1 (es)	1981-08-16
YU236180A (en)	1983-01-21
AU518068B2 (en)	1981-09-10

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: PFIZER INC.

Publication	Publication Date	Title
US4024179A (en)	1977-05-17	Substituted ω-pentanorprostaglandins
CH647222A5 (de)	1985-01-15	9-desoxy-9a-methylen-isostere von pgi-2 und verfahren zu deren herstellung.
US4011262A (en)	1977-03-08	13,14-Dihydro-15-substituted-ω-pentanorprostaglandins of the two series
US4022794A (en)	1977-05-10	Novel analogs of prostaglandins with 4-oxo-thiazolidinyl nucleus and method of preparation thereof
NO147836B (no)	1983-03-14	Nye 16-aryloksy-substituerte omega-tetranorprostaglandiner for anvendelse som fruktbarhetsregulerende middel, svangerskapsavbrytende middel eller middel for synkronisering av brunstcyklusen hos husdyr
US4102888A (en)	1978-07-25	3-Thiazolidinyl heptanoic acids
Schaaf et al.	1981	N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants
DE2626888C2 (de)	1982-05-06	Optisch aktive 11-Desoxy-16-aryloxy-&omega;-tetranorprostaglandine, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen, die diese Verbindungen enthalten
FI68615B (fi)	1985-06-28	Foerfarande foer framstaellning av terapeutiskt anvaendbara 15sulfonamidprostaglandinderivat
CA1041495A (en)	1978-10-31	Process for preparing a 15-substituted-w-pentanorprostaglandins
NO763451L (es)	1977-04-22
CH634831A5 (en)	1983-02-28	Process for the preparation of optically active or racemic prostaglandins.
DE2737808A1 (de)	1978-03-16	2-substituierte aryl-heterocyclische omega-pentanorprostaglandine
US4404372A (en)	1983-09-13	15-Substituted-ω-pentanorprostaglandin derivatives
DE2550004A1 (de)	1977-05-18	Thiaprostaglandine
DE2606051A1 (de)	1976-09-02	2,2-difluor-prostaglandin-e, -f tief alpha, -f tief beta, -a und -b-analoga und verfahren zu deren herstellung
DE2737807A1 (de)	1978-03-09	C tief 1 -p-biphenylester von omega-pentanorprostaglandinen
KR950005775B1 (ko)	1995-05-30	4-하이드록시-4-(치환된 알케닐)사이클로헥산 카복실산
US4204074A (en)	1980-05-20	16-Substituted prostaglandins
US4036832A (en)	1977-07-19	15-Substituted-ω-pentanorprostaglandins
US3935261A (en)	1976-01-27	Cyclopentane derivatives
US4258053A (en)	1981-03-24	Thienyl-prostaglandins and process for their manufacture
US4292444A (en)	1981-09-29	Sulfonyl prostaglandin carboxamide derivatives
FI70885C (fi)	1986-10-27	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 16-amino-18,19,20-trinor-prostaglandinderivat och framstaellning av deras syraadditionssalter
US4342868A (en)	1982-08-03	2-Descarboxy-2-(tetrazol-5-yl)-16,16-dimethyl-17-(2-furyl)-ω-trisnorprostaglandin E2