NO770864L - Fremgangsm}te for fremstilling av cyklopenta(b)tiofenderivater - Google Patents

Fremgangsm}te for fremstilling av cyklopenta(b)tiofenderivater

Info

Publication number: NO770864L
Authority: NO; Norway
Prior art keywords: formula; cyclopenta; ethyl; dihydro; acid
Prior art date: 1976-03-12

Application number

NO770864A

Other languages

English (en)

Norwegian (no)

Inventor

Jean-Marie Teulon

Original Assignee

Hexachimie

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-03-12

Filing date

1977-03-11

Publication date

1977-09-13

1977-03-11 Application filed by Hexachimie filed Critical Hexachimie

1977-09-13 Publication of NO770864L publication Critical patent/NO770864L/no

Links

238000000034 method Methods 0.000 title claims description 34
238000002360 preparation method Methods 0.000 title description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 75
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 22
-1 dimethylaminoethyl Chemical group 0.000 claims description 20
238000010992 reflux Methods 0.000 claims description 18
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
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 claims description 8
125000004494 ethyl ester group Chemical group 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
150000002825 nitriles Chemical class 0.000 claims description 6
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
238000002844 melting Methods 0.000 claims description 5
230000008018 melting Effects 0.000 claims description 5
150000001414 amino alcohols Chemical class 0.000 claims description 4
125000004103 aminoalkyl group Chemical group 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
230000001476 alcoholic effect Effects 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
150000003973 alkyl amines Chemical class 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical class CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 5
231100000252 nontoxic Toxicity 0.000 claims 3
230000003000 nontoxic effect Effects 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
230000003301 hydrolyzing effect Effects 0.000 claims 2
239000003513 alkali Substances 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
229910017053 inorganic salt Inorganic materials 0.000 claims 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 claims 1
125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
150000003385 sodium Chemical class 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
239000000243 solution Substances 0.000 description 31
239000013078 crystal Substances 0.000 description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 24
239000000203 mixture Substances 0.000 description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
239000012346 acetyl chloride Substances 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
235000011054 acetic acid Nutrition 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
239000007788 liquid Substances 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
229960002887 deanol Drugs 0.000 description 4
239000012071 phase Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000005904 alkaline hydrolysis reaction Methods 0.000 description 3
238000006114 decarboxylation reaction Methods 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
HEJCFABXDJTVNU-UHFFFAOYSA-N 5-ethyl-5,6-dihydro-4h-cyclopenta[b]thiophene Chemical compound C1=CSC2=C1CC(CC)C2 HEJCFABXDJTVNU-UHFFFAOYSA-N 0.000 description 2
RCHCPZUIXUSCLQ-UHFFFAOYSA-N 5-propan-2-yl-4,5-dihydrocyclopenta[b]thiophen-6-one Chemical compound C1=CSC2=C1CC(C(C)C)C2=O RCHCPZUIXUSCLQ-UHFFFAOYSA-N 0.000 description 2
YHUCZDMXOKEWKN-UHFFFAOYSA-N 5-propan-2-yl-5,6-dihydro-4h-cyclopenta[b]thiophene-2-carbaldehyde Chemical compound C1=C(C=O)SC2=C1CC(C(C)C)C2 YHUCZDMXOKEWKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
229940113118 carrageenan Drugs 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
239000000679 carrageenan Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
150000002691 malonic acids Chemical class 0.000 description 2
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
238000005303 weighing Methods 0.000 description 2
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 2
NWEQYIVZWWGGOX-UHFFFAOYSA-N 1-sulfanylidene-1,3-thiazolidine Chemical compound S=S1CCNC1 NWEQYIVZWWGGOX-UHFFFAOYSA-N 0.000 description 1
OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
KVPBSBOTFRNKOM-UHFFFAOYSA-N 2h-cyclopenta[b]thiophene Chemical class C1=CC2=CCSC2=C1 KVPBSBOTFRNKOM-UHFFFAOYSA-N 0.000 description 1
QHZITEHQKWPDJE-UHFFFAOYSA-N 4,5-dihydrocyclopenta[b]thiophen-6-one Chemical class C1=CSC2=C1CCC2=O QHZITEHQKWPDJE-UHFFFAOYSA-N 0.000 description 1
HVFDFIUWSIWARD-UHFFFAOYSA-N 5-ethyl-4,5-dihydrocyclopenta[b]thiophen-6-one Chemical compound C1=CSC2=C1CC(CC)C2=O HVFDFIUWSIWARD-UHFFFAOYSA-N 0.000 description 1
GMXGJMCXYQGWEU-UHFFFAOYSA-N 5-ethyl-5,6-dihydro-4h-cyclopenta[b]thiophene-2-carbaldehyde Chemical compound C1=C(C=O)SC2=C1CC(CC)C2 GMXGJMCXYQGWEU-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
238000006214 Clemmensen reduction reaction Methods 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
230000003356 anti-rheumatic effect Effects 0.000 description 1
239000003435 antirheumatic agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
239000006071 cream 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000005646 oximino group Chemical group 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000002265 prevention Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO770864A 1976-03-12 1977-03-11 Fremgangsm}te for fremstilling av cyklopenta(b)tiofenderivater NO770864L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB10049/76A GB1544963A (en)	1976-03-12	1976-03-12	Cyclopenta(b)thiophene derivatives

Publications (1)

Publication Number	Publication Date
NO770864L true NO770864L (no)	1977-09-13

Family

ID=9960512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO770864A NO770864L (no)	1976-03-12	1977-03-11	Fremgangsm}te for fremstilling av cyklopenta(b)tiofenderivater

Country Status (16)

Country	Link
US (1)	US4122091A (de)
JP (1)	JPS52111561A (de)
AR (1)	AR212755A1 (de)
AT (1)	ATA160977A (de)
AU (1)	AU506384B2 (de)
BE (1)	BE852375A (de)
DD (1)	DD129909A5 (de)
DE (1)	DE2709295A1 (de)
DK (1)	DK106377A (de)
ES (1)	ES456639A1 (de)
FR (1)	FR2346348A1 (de)
GB (1)	GB1544963A (de)
NL (1)	NL7702681A (de)
NO (1)	NO770864L (de)
PT (1)	PT66276B (de)
SE (1)	SE7702166L (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5740478A (en) *	1980-08-22	1982-03-06	Ono Pharmaceut Co Ltd	Rhodanine derivative, its preparation and aldose reductase inhibitor containing rhodanine derivative
FR2578845B1 (fr) *	1985-03-12	1987-05-22	Roussel Uclaf	Nouveaux derives de l'acide thiophene acetique, leur procede de preparation, les intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant
IT1404379B1 (it) *	2011-02-11	2013-11-22	Lembo	Eterocicli ad attivita' antiipertensiva

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH540247A (de) *	1967-04-21	1973-09-28	Ciba Geigy Ag	Verfahren zur Herstellung von heterocyclischen, Asthylendoppelbindungen enthaltenden Verbindungen
NO743135L (de) *	1973-09-11	1975-04-07	Sandoz Ag

1976
- 1976-03-12 GB GB10049/76A patent/GB1544963A/en not_active Expired
1977
- 1977-02-17 FR FR7704599A patent/FR2346348A1/fr active Granted
- 1977-02-28 SE SE7702166A patent/SE7702166L/xx unknown
- 1977-03-03 DE DE19772709295 patent/DE2709295A1/de active Pending
- 1977-03-07 AR AR266767A patent/AR212755A1/es active
- 1977-03-08 PT PT66276A patent/PT66276B/pt unknown
- 1977-03-08 US US05/775,534 patent/US4122091A/en not_active Expired - Lifetime
- 1977-03-08 ES ES456639A patent/ES456639A1/es not_active Expired
- 1977-03-10 AU AU23150/77A patent/AU506384B2/en not_active Expired
- 1977-03-10 JP JP2658877A patent/JPS52111561A/ja active Pending
- 1977-03-10 AT AT160977A patent/ATA160977A/de not_active IP Right Cessation
- 1977-03-11 NL NL7702681A patent/NL7702681A/xx not_active Application Discontinuation
- 1977-03-11 DK DK106377A patent/DK106377A/da unknown
- 1977-03-11 BE BE2055728A patent/BE852375A/xx unknown
- 1977-03-11 NO NO770864A patent/NO770864L/no unknown
- 1977-03-14 DD DD7700197843A patent/DD129909A5/de unknown

Also Published As

Publication number	Publication date
FR2346348B1 (de)	1978-11-03
AR212755A1 (es)	1978-09-29
PT66276A (fr)	1977-04-01
PT66276B (fr)	1978-08-08
NL7702681A (nl)	1977-09-14
US4122091A (en)	1978-10-24
AU2315077A (en)	1978-09-14
GB1544963A (en)	1979-04-25
ES456639A1 (es)	1978-02-01
AU506384B2 (en)	1979-12-20
JPS52111561A (en)	1977-09-19
BE852375A (fr)	1977-07-01
DK106377A (da)	1977-09-13
FR2346348A1 (fr)	1977-10-28
DE2709295A1 (de)	1977-09-15
SE7702166L (sv)	1977-09-13
ATA160977A (de)	1980-01-15
DD129909A5 (de)	1978-02-15

Publication	Publication Date	Title
US4110337A (en)	1978-08-29	Triazolobenzodiazepines
NO760993L (de)	1976-09-21
CS249539B2 (en)	1987-03-12	Method of 3-substituted 2-oxindole-carboxamides production
IE73223B1 (en)	1997-05-07	2-thienylglycidic acid derivative process for its preparation and its use as synthetic intermediate
NO164476B (no)	1990-07-02	Analogifremgangsmaate ved fremstilling av terapeutisk virksomme 1,2,3,5-tetrahydroimidazo-(2,1-b)-kinazoliner.
NO152048B (no)	1985-04-15	Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive 5h-2,3-benzodiazepinderivater
NO154346B (no)	1986-05-26	Analogifremgangsmaate for fremstilling av terapeutisk aktive ftalazin-4-yl-eddiksyrederivater.
NO154554B (no)	1986-07-07	Fremgangsmaate til fremstilling av armeringsfibre for mineralske byggematerialer.
US3484445A (en)	1969-12-16	Derivatives of chromone-2-carboxylic acid
NO874834L (no)	1988-05-24	Fremgangsmaate for fremstilling av terapeutisk aktive tienopyridinoner.
CA1113114A (en)	1981-11-24	Cycloalkylidenemethylphenylacetic acid derivatives
PL145230B1 (en)	1988-08-31	Method of obtaining novel 2-ketoindolo-1-carbonamides
NO153001B (no)	1985-09-23	Drivanordning for skip
NZ225378A (en)	1992-03-26	Tetrazole derivatives and pharmaceutical compositions
US2489236A (en)	1949-11-22	Synthesis of biotin and related compounds
NO761303L (de)	1976-10-19
DK156661B (da)	1989-09-18	Analogifremgangsmaade til fremstilling af 1-azaxanton-3-karboxylsyrer
NO770864L (no)	1977-09-13	Fremgangsm}te for fremstilling av cyklopenta(b)tiofenderivater
NO140821B (no)	1979-08-13	Analogifremgangsmaate ved fremstilling av terapeutisk aktive pyrido-pyrimidin-derivater
US3414582A (en)	1968-12-03	4-(dialkylaminoethoxyphenyl) pyrazoles
KR860001874B1 (ko)	1986-10-24	2-옥스인돌-1-카복스 아미드의 제조방법
US4420476A (en)	1983-12-13	Benzofuro[3,2-c]pyrazol-3-amine derivatives
NO161675B (no)	1989-06-05	Analogifremgangsmaate for fremstilling av terapeutisk aktive benzoyl-pyrrolo(1,2-a) pyrrol-karboksylsyrederivater.
NO131930B (de)	1975-05-20
US4161599A (en)	1979-07-17	Process for the preparation of thieno(2,3-c)- and thieno(3,2-c)pyridines