NO760297L - - Google Patents

Info

Publication number: NO760297L
Authority: NO; Norway
Prior art keywords: formula; dihydrodibenzo; thiepin; acid; salt
Prior art date: 1975-02-18

Application number

NO760297A

Other languages

English (en)

Norwegian (no)

Inventor

J Ackrell

Original Assignee

Syntex Inc

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.)

1975-02-18

Filing date

1976-01-30

Publication date

1976-08-19

1975-11-21 Priority claimed from US05/634,085 external-priority patent/US4000288A/en

1975-11-21 Priority claimed from US05/634,086 external-priority patent/US4000308A/en

1976-01-30 Application filed by Syntex Inc filed Critical Syntex Inc

1976-08-19 Publication of NO760297L publication Critical patent/NO760297L/no

Links

XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 141
239000002253 acid Substances 0.000 claims description 127
150000001875 compounds Chemical class 0.000 claims description 102
150000003839 salts Chemical class 0.000 claims description 79
150000002148 esters Chemical class 0.000 claims description 67
235000019260 propionic acid Nutrition 0.000 claims description 64
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 64
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 38
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
239000001257 hydrogen Substances 0.000 claims description 37
-1 isoamyl ester Chemical class 0.000 claims description 33
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 26
238000006243 chemical reaction Methods 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 24
238000000034 method Methods 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 23
206010061218 Inflammation Diseases 0.000 claims description 15
230000004054 inflammatory process Effects 0.000 claims description 15
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
241000124008 Mammalia Species 0.000 claims description 12
208000002193 Pain Diseases 0.000 claims description 10
230000036407 pain Effects 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
238000006460 hydrolysis reaction Methods 0.000 claims description 9
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 8
206010037660 Pyrexia Diseases 0.000 claims description 8
159000000000 sodium salts Chemical class 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 7
239000011575 calcium Substances 0.000 claims description 7
229910052791 calcium Inorganic materials 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
230000007062 hydrolysis Effects 0.000 claims description 7
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 7
206010000234 Abortion spontaneous Diseases 0.000 claims description 6
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 claims description 6
208000036029 Uterine contractions during pregnancy Diseases 0.000 claims description 6
159000000007 calcium salts Chemical class 0.000 claims description 6
150000001879 copper Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
208000000995 spontaneous abortion Diseases 0.000 claims description 6
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
150000004702 methyl esters Chemical class 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 4
208000005107 Premature Birth Diseases 0.000 claims description 4
206010036590 Premature baby Diseases 0.000 claims description 4
238000005809 transesterification reaction Methods 0.000 claims description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
229910052802 copper Inorganic materials 0.000 claims description 3
239000010949 copper Substances 0.000 claims description 3
208000015994 miscarriage Diseases 0.000 claims description 3
230000004118 muscle contraction Effects 0.000 claims description 3
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
238000007069 methylation reaction Methods 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 22
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 4
208000037805 labour Diseases 0.000 claims 2
241000282341 Mustela putorius furo Species 0.000 claims 1
230000003111 delayed effect Effects 0.000 claims 1
210000000754 myometrium Anatomy 0.000 claims 1
230000006340 racemization Effects 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
239000000243 solution Substances 0.000 description 49
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 48
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
239000000203 mixture Substances 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
235000019441 ethanol Nutrition 0.000 description 19
239000002904 solvent Substances 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000003960 organic solvent Substances 0.000 description 13
238000010992 reflux Methods 0.000 description 13
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
239000007787 solid Substances 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
239000004615 ingredient Substances 0.000 description 11
239000000126 substance Substances 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
230000003110 anti-inflammatory effect Effects 0.000 description 8
WGRYDTFDVJDMCG-UHFFFAOYSA-N dipropan-2-yl 2-nitrobenzene-1,4-dicarboxylate Chemical compound CC(C)OC(=O)C1=CC=C(C(=O)OC(C)C)C([N+]([O-])=O)=C1 WGRYDTFDVJDMCG-UHFFFAOYSA-N 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
229910052700 potassium Inorganic materials 0.000 description 8
239000011591 potassium Substances 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
239000013543 active substance Substances 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 7
239000000284 extract Substances 0.000 description 7
210000002683 foot Anatomy 0.000 description 7
239000007903 gelatin capsule Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
229910000019 calcium carbonate Inorganic materials 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
210000003754 fetus Anatomy 0.000 description 6
239000003921 oil Substances 0.000 description 6
230000035935 pregnancy Effects 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
241000700159 Rattus Species 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
HRXCTGGMTOEWFE-UHFFFAOYSA-N dipropan-2-yl 2-benzylsulfanylbenzene-1,4-dicarboxylate Chemical compound CC(C)OC(=O)C1=CC=C(C(=O)OC(C)C)C(SCC=2C=CC=CC=2)=C1 HRXCTGGMTOEWFE-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
159000000003 magnesium salts Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
YMDCGVVDZQFCPH-UHFFFAOYSA-N 2-benzylsulfanylterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(SCC=2C=CC=CC=2)=C1 YMDCGVVDZQFCPH-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000008901 benefit Effects 0.000 description 4
230000037396 body weight Effects 0.000 description 4
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 4
229960001231 choline Drugs 0.000 description 4
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
229960002895 phenylbutazone Drugs 0.000 description 4
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000000829 suppository Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
208000010392 Bone Fractures Diseases 0.000 description 3
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical class [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
229940025084 amphetamine Drugs 0.000 description 3
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 3
229960001948 caffeine Drugs 0.000 description 3
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 3
239000000679 carrageenan Substances 0.000 description 3
235000010418 carrageenan Nutrition 0.000 description 3
229920001525 carrageenan Polymers 0.000 description 3
229940113118 carrageenan Drugs 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 3
230000008602 contraction Effects 0.000 description 3
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 3
239000001095 magnesium carbonate Substances 0.000 description 3
229910000021 magnesium carbonate Inorganic materials 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000006187 pill Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 3
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
229960000281 trometamol Drugs 0.000 description 3
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 2
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
229940013085 2-diethylaminoethanol Drugs 0.000 description 2
NGDNVOAEIVQRFH-UHFFFAOYSA-N 2-nonanol Chemical compound CCCCCCCC(C)O NGDNVOAEIVQRFH-UHFFFAOYSA-N 0.000 description 2
239000004475 Arginine Substances 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
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GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 description 1
229910021506 iron(II) hydroxide Inorganic materials 0.000 description 1
NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
210000005067 joint tissue Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000003902 lesion Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000006210 lotion Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229940087646 methanolamine Drugs 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
230000003387 muscular Effects 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
DISPOJHKKXSCLS-UHFFFAOYSA-N n-diaminophosphorylmethanamine Chemical compound CNP(N)(N)=O DISPOJHKKXSCLS-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229940100692 oral suspension Drugs 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000006174 pH buffer Substances 0.000 description 1
JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
239000002002 slurry Substances 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000000050 smooth muscle relaxant Substances 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
AYGJDUHQRFKLBG-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;dihydrate Chemical compound O.O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 AYGJDUHQRFKLBG-UHFFFAOYSA-M 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
XPSQRFGOPLDGPO-UHFFFAOYSA-N sodium;dimethylazanide Chemical compound [Na+].C[N-]C XPSQRFGOPLDGPO-UHFFFAOYSA-N 0.000 description 1
JXHZRQHZVYDRGX-UHFFFAOYSA-M sodium;hydrogen sulfate;hydrate Chemical compound [OH-].[Na+].OS(O)(=O)=O JXHZRQHZVYDRGX-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
229940035044 sorbitan monolaurate Drugs 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
229940117013 triethanolamine oleate Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
229940057402 undecyl alcohol Drugs 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO760297A 1975-02-18 1976-01-30 NO760297L (de)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US55031675A	1975-02-18	1975-02-18
US59172575A	1975-06-30	1975-06-30
US05/634,085 US4000288A (en)	1975-02-18	1975-11-21	6,11-dihydrodibenzo-thiepin-11-ones, compositions and uses thereof
US05/634,086 US4000308A (en)	1975-02-18	1975-11-21	6,11-Dihydrodibenzo-thiepin-11-ones, compositions and uses thereof

Publications (1)

Publication Number	Publication Date
NO760297L true NO760297L (de)	1976-08-19

Family

ID=27504746

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO760297A NO760297L (de)	1975-02-18	1976-01-30

Country Status (16)

Country	Link
JP (1)	JPS51143688A (de)
AR (1)	AR216050A1 (de)
AT (1)	AT352731B (de)
AU (1)	AU500501B2 (de)
BE (1)	BE838637A (de)
DE (1)	DE2606312A1 (de)
DK (1)	DK67676A (de)
ES (2)	ES459401A1 (de)
FI (1)	FI760273A7 (de)
FR (1)	FR2301245A1 (de)
GB (1)	GB1505085A (de)
IL (1)	IL48807A0 (de)
NL (1)	NL7600899A (de)
NO (1)	NO760297L (de)
PT (1)	PT64692B (de)
SE (1)	SE7601754L (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4130654A (en) *	1978-01-30	1978-12-19	Syntex (U.S.A.) Inc.	Novel 4-(8X-6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)-4-oxobutyric acids, methods of preparation, compositions and uses thereof
TW200615273A (en)	2004-11-10	2006-05-16	Nicholas Piramal India Ltd	Fused tricyclic compounds as inhibitors of tumor necrosis factor-alpha

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI258574A7 (de) *	1973-09-13	1975-03-14	Sandoz Ag

1976
- 1976-01-08 IL IL48807A patent/IL48807A0/xx unknown
- 1976-01-14 PT PT64692A patent/PT64692B/pt unknown
- 1976-01-16 GB GB1783/76A patent/GB1505085A/en not_active Expired
- 1976-01-29 NL NL7600899A patent/NL7600899A/xx not_active Application Discontinuation
- 1976-01-30 NO NO760297A patent/NO760297L/no unknown
- 1976-01-30 AU AU10686/76A patent/AU500501B2/en not_active Expired
- 1976-02-04 AR AR262140A patent/AR216050A1/es active
- 1976-02-05 FI FI760273A patent/FI760273A7/fi not_active Application Discontinuation
- 1976-02-17 DE DE19762606312 patent/DE2606312A1/de active Pending
- 1976-02-17 JP JP51016446A patent/JPS51143688A/ja active Pending
- 1976-02-17 BE BE164382A patent/BE838637A/xx unknown
- 1976-02-17 FR FR7604353A patent/FR2301245A1/fr active Granted
- 1976-02-17 SE SE7601754A patent/SE7601754L/xx unknown
- 1976-02-18 DK DK67676*#A patent/DK67676A/da unknown
- 1976-02-18 AT AT115976A patent/AT352731B/de not_active IP Right Cessation
1977
- 1977-06-01 ES ES459401A patent/ES459401A1/es not_active Expired
- 1977-06-01 ES ES459400A patent/ES459400A1/es not_active Expired

Also Published As

Publication number	Publication date
GB1505085A (en)	1978-03-22
SE7601754L (sv)	1976-10-25
ATA115976A (de)	1979-03-15
NL7600899A (nl)	1976-08-20
JPS51143688A (en)	1976-12-10
DE2606312A1 (de)	1976-08-26
AU1068676A (en)	1977-08-04
PT64692A (fr)	1976-02-01
ES459400A1 (es)	1978-08-16
PT64692B (fr)	1978-01-04
FI760273A7 (de)	1976-08-19
BE838637A (fr)	1976-08-17
IL48807A0 (en)	1976-03-31
FR2301245B1 (de)	1979-07-20
DK67676A (da)	1976-08-19
AU500501B2 (en)	1979-05-24
AR216050A1 (es)	1979-11-30
FR2301245A1 (fr)	1976-09-17
AT352731B (de)	1979-10-10
ES459401A1 (es)	1979-06-16

Publication	Publication Date	Title
EP0253500B1 (de)	1991-02-27	Acylanilidabkömmlinge
US3654349A (en)	1972-04-04	Substituted indenyl acetic acids
ES2703280T3 (es)	2019-03-07	Proceso de preparación y purificación de ácidos grasos
JPS647997B2 (de)	1989-02-10
US3836516A (en)	1974-09-17	Diazo derivatives of antibiotic x-537a
KR850000609B1 (ko)	1985-05-01	5-벤조일-6-클로로(또는 브로모)-1,2-디히드로-3H-피롤로[1,2-a]피롤-1-카르복실산 유도체의 제조방법
US4104280A (en)	1978-08-01	Dibenzo [b.f]thiepin and dibenzo[b.f]oxepin derivatives
Wendler et al.	1952	The Synthesis of 11-Hydroxylated Cortical Steroids. 17-Hydroxycorticosterone1
FR2574794A1 (fr)	1986-06-20	Analogues de prostaglandines tetrahydrothienyl-substitues a action cardiovasculaire
US4166177A (en)	1979-08-28	Substituted 2,2-dioxo-1,2,3-benzoxathiazines
US4057641A (en)	1977-11-08	Method of treating inflammation with 2-(2,3-dihydro-2-isopropyl-4-oxo-4H-1-benzopyran-6-yl)propionic acid
KR0129526B1 (ko)	1998-04-09	(rs)-2-(2,3-디히드로-5-히드록시-4,6,7-트리메틸벤조푸라닐)아세트산 및 2-(2,3-디히드로-5-아실옥시-4,6,7-트리메틸벤조푸라닐)아세트산 및 이들의 에스테르, 점액 조절제 및 안티히스케믹 약제로서 이들의 용도, 그리고 이들의 제조방법
HU200450B (en)	1990-06-28	Process for production of derivatives of aroil-benzofurane and benzotiophen acetic acid and prophionic acid
US4151179A (en)	1979-04-24	2-(4H-1-Benzopyran-6-yl)propionic acids
US3892769A (en)	1975-07-01	Acetaminophen esters of aryl salicylic acids
SU1072801A3 (ru)	1984-02-07	Способ получени производных простациклина или их эпимеров
US4221790A (en)	1980-09-09	Substituted 2,2-dioxo-1,2,3-benzoxathiazines
FR2581997A1 (fr)	1986-11-21	Analogues de prostaglandines a substituant thiabicycloheptane, a proprietes therapeutiques
US4000308A (en)	1976-12-28	6,11-Dihydrodibenzo-thiepin-11-ones, compositions and uses thereof
US4000288A (en)	1976-12-28	6,11-dihydrodibenzo-thiepin-11-ones, compositions and uses thereof
JPS6254110B2 (de)	1987-11-13
EP0337885B1 (de)	1993-03-17	Trienische Derivate mit chromenischer Struktur, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammenstellungen
Cisney et al.	1954	Conidendrin. II. 1 The Stereochemistry and Reactions of the Lactone Ring2
US4051149A (en)	1977-09-27	6,11-Dihydrodibenzo-[b.e.]-thiepin-11-one-3-acetonitrile
US3450698A (en)	1969-06-17	Phenthiazine derivatives