HU177226B - Process for preparing 5-/substituted/-2-indane-carboxylic acid derivatives - Google Patents

Process for preparing 5-/substituted/-2-indane-carboxylic acid derivatives Download PDF

Info

Publication number: HU177226B
Authority: HU; Hungary
Prior art keywords: formula; substituted; ppm; compound; proton
Prior art date: 1976-12-14

Application number

HU77LI316A

Other languages

English (en)

Hungarian (hu)

Inventor

Michel Bayssat

Francis Sautel

Jean-Claude Depin

Annie Betbeder-Matibet

Original Assignee

Lipha

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.)

1976-12-14

Filing date

1977-12-13

Publication date

1981-08-28

1977-12-13 Application filed by Lipha filed Critical Lipha

1981-08-28 Publication of HU177226B publication Critical patent/HU177226B/hu

Links

238000004519 manufacturing process Methods 0.000 title claims 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 24
-1 5- (substituted) -2-indanecarboxylic acids Chemical class 0.000 claims description 18
238000004458 analytical method Methods 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 12
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229960003280 cupric chloride Drugs 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 2
239000012954 diazonium Substances 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
JBQMFBWTKWOSQX-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)CCC2=C1 JBQMFBWTKWOSQX-UHFFFAOYSA-N 0.000 claims 2
BODTUSQBETVWIB-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)CCC2=C1 BODTUSQBETVWIB-UHFFFAOYSA-N 0.000 claims 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
206010029897 Obsessive thoughts Diseases 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical class C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
125000003118 aryl group Chemical group 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
239000000203 mixture Substances 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 15
239000007787 solid Substances 0.000 description 15
239000000460 chlorine Substances 0.000 description 14
238000002329 infrared spectrum Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 13
239000000243 solution Substances 0.000 description 11
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
238000010992 reflux Methods 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
239000002253 acid Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000000034 method Methods 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
230000003110 anti-inflammatory effect Effects 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
206010030113 Oedema Diseases 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
RMOPJLIMRSAIMD-UHFFFAOYSA-N methyl 2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=CC=C2CC(C(=O)OC)CC2=C1 RMOPJLIMRSAIMD-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
208000011580 syndromic disease Diseases 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
102000008186 Collagen Human genes 0.000 description 2
108010035532 Collagen Proteins 0.000 description 2
206010015150 Erythema Diseases 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
230000001760 anti-analgesic effect Effects 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
229920001436 collagen Polymers 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
239000008098 formaldehyde solution Substances 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
QIBSLMQIRSKXMN-UHFFFAOYSA-N methyl 5-(4-aminobenzoyl)-2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=C2CC(C(=O)OC)CC2=CC=C1C(=O)C1=CC=C(N)C=C1 QIBSLMQIRSKXMN-UHFFFAOYSA-N 0.000 description 2
KUSFRNJBKHKRMW-UHFFFAOYSA-N methyl 5-(4-chlorosulfonylbenzoyl)-2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=C2CC(C(=O)OC)CC2=CC=C1C(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 KUSFRNJBKHKRMW-UHFFFAOYSA-N 0.000 description 2
KFUAGWZOTUVYQI-UHFFFAOYSA-N methyl 5-[4-(dimethylamino)benzoyl]-2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=C2CC(C(=O)OC)CC2=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 KFUAGWZOTUVYQI-UHFFFAOYSA-N 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000002244 precipitate Chemical group 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
LGTZRESQDNRCAZ-UHFFFAOYSA-N 1-benzoyl-2,3-dihydro-1H-indene-2-carboxylic acid Chemical compound C(C1=CC=CC=C1)(=O)C1C(CC2=CC=CC=C12)C(=O)O LGTZRESQDNRCAZ-UHFFFAOYSA-N 0.000 description 1
VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
QOUPJXLLBHPYEV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine;hypochlorous acid Chemical compound ClO.CCN(CC)CCCl QOUPJXLLBHPYEV-UHFFFAOYSA-N 0.000 description 1
KTUOJDXAHZOFCA-UHFFFAOYSA-N 3-(diethylamino)propanamide Chemical class CCN(CC)CCC(N)=O KTUOJDXAHZOFCA-UHFFFAOYSA-N 0.000 description 1
AJSVPEVDFBYRCH-UHFFFAOYSA-N 3-methylthiophene-2-carbonyl chloride Chemical compound CC=1C=CSC=1C(Cl)=O AJSVPEVDFBYRCH-UHFFFAOYSA-N 0.000 description 1
AJBWNNKDUMXZLM-UHFFFAOYSA-N 4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C=C1 AJBWNNKDUMXZLM-UHFFFAOYSA-N 0.000 description 1
AMCNMIOZHLTSTI-UHFFFAOYSA-N 5-(2,5-dichlorobenzoyl)-2,3-dihydro-1h-indene-2-carbonyl chloride Chemical compound C1=C2CC(C(=O)Cl)CC2=CC=C1C(=O)C1=CC(Cl)=CC=C1Cl AMCNMIOZHLTSTI-UHFFFAOYSA-N 0.000 description 1
STZNWHRZVBVEHD-UHFFFAOYSA-N 5-(4-methylsulfonylbenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1=CC=C(CC(C2)C(O)=O)C2=C1 STZNWHRZVBVEHD-UHFFFAOYSA-N 0.000 description 1
QYMSNCHUHPSGTR-UHFFFAOYSA-N 5-[4-(dimethylamino)benzoyl]-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(CC(C2)C(O)=O)C2=C1 QYMSNCHUHPSGTR-UHFFFAOYSA-N 0.000 description 1
WOAAHXNXOSCQFP-UHFFFAOYSA-N 5-benzoyl-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=C2CC(C(=O)O)CC2=CC=C1C(=O)C1=CC=CC=C1 WOAAHXNXOSCQFP-UHFFFAOYSA-N 0.000 description 1
ZURUVZFDEVKNCE-UHFFFAOYSA-N 5-methylfuran-2-carbonyl chloride Chemical compound CC1=CC=C(C(Cl)=O)O1 ZURUVZFDEVKNCE-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
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150000004781 alginic acids Chemical class 0.000 description 1
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230000000202 analgesic effect Effects 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
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239000003795 chemical substances by application Substances 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical group CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
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238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
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LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
DIETYQFOVVDBLF-UHFFFAOYSA-N ethyl 5-(4-acetamidobenzoyl)-2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=C2CC(C(=O)OCC)CC2=CC=C1C(=O)C1=CC=C(NC(C)=O)C=C1 DIETYQFOVVDBLF-UHFFFAOYSA-N 0.000 description 1
CEDKAUHEEJPZMM-UHFFFAOYSA-N ethyl acetate;octane Chemical compound CCOC(C)=O.CCCCCCCC CEDKAUHEEJPZMM-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
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238000000265 homogenisation Methods 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
150000002468 indanes Chemical class 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
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150000004702 methyl esters Chemical class 0.000 description 1
239000013588 oral product Substances 0.000 description 1
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239000012074 organic phase Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
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229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
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230000003595 spectral effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
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 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
- 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
- C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
- 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]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- 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

Landscapes

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

HU77LI316A 1976-12-14 1977-12-13 Process for preparing 5-/substituted/-2-indane-carboxylic acid derivatives HU177226B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7637574A FR2374032A2 (fr)	1976-12-14	1976-12-14	Nouveaux acides carboxyliques derives de l'indane

Publications (1)

Publication Number	Publication Date
HU177226B true HU177226B (en)	1981-08-28

Family

ID=9181028

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU77LI316A HU177226B (en)	1976-12-14	1977-12-13	Process for preparing 5-/substituted/-2-indane-carboxylic acid derivatives

Country Status (21)

Country	Link
JP (1)	JPS5373548A (de)
AT (1)	AT355559B (de)
AU (1)	AU515268B2 (de)
BE (1)	BE861826R (de)
CA (1)	CA1088554A (de)
CH (1)	CH627728A5 (de)
DD (1)	DD133323A6 (de)
DE (1)	DE2753315A1 (de)
DK (1)	DK144640C (de)
ES (1)	ES465056A2 (de)
FR (1)	FR2374032A2 (de)
GB (1)	GB1584298A (de)
HU (1)	HU177226B (de)
IE (1)	IE46013B1 (de)
IL (2)	IL60599A0 (de)
MX (1)	MX4954E (de)
NL (1)	NL7713876A (de)
NO (1)	NO774285L (de)
SE (1)	SE436740B (de)
SU (1)	SU799646A3 (de)
ZA (1)	ZA777438B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5746334B2 (ja) *	2010-06-16	2015-07-08	シマベイセラピューティクス，インコーポレーテッド	Ｇｐｒ１２０受容体作動薬及びその使用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4980053A (de) *	1972-12-05	1974-08-02
JPS5838416B2 (ja) *	1974-05-31	1983-08-23	武田薬品工業株式会社	カンジヨウカゴウブツノセイゾウホウ
JPS5335944B2 (de) *	1974-05-21	1978-09-29

1976
- 1976-12-14 FR FR7637574A patent/FR2374032A2/fr active Granted
1977
- 1977-11-30 DE DE19772753315 patent/DE2753315A1/de not_active Ceased
- 1977-12-12 GB GB51699/77A patent/GB1584298A/en not_active Expired
- 1977-12-13 IE IE2520/77A patent/IE46013B1/en unknown
- 1977-12-13 SE SE7714110A patent/SE436740B/sv unknown
- 1977-12-13 NO NO774285A patent/NO774285L/no unknown
- 1977-12-13 DK DK554677A patent/DK144640C/da not_active IP Right Cessation
- 1977-12-13 HU HU77LI316A patent/HU177226B/hu unknown
- 1977-12-13 DD DD7700202588A patent/DD133323A6/de unknown
- 1977-12-13 MX MX776686U patent/MX4954E/es unknown
- 1977-12-14 NL NL7713876A patent/NL7713876A/xx not_active Application Discontinuation
- 1977-12-14 CH CH1541077A patent/CH627728A5/fr not_active IP Right Cessation
- 1977-12-14 JP JP14943377A patent/JPS5373548A/ja active Pending
- 1977-12-14 BE BE183429A patent/BE861826R/xx not_active IP Right Cessation
- 1977-12-14 ES ES465056A patent/ES465056A2/es not_active Expired
- 1977-12-14 ZA ZA00777438A patent/ZA777438B/xx unknown
- 1977-12-14 AU AU31530/77A patent/AU515268B2/en not_active Expired
- 1977-12-14 CA CA293,076A patent/CA1088554A/fr not_active Expired
- 1977-12-14 AT AT892577A patent/AT355559B/de not_active IP Right Cessation
1979
- 1979-04-06 SU SU792746906A patent/SU799646A3/ru active
1980
- 1980-07-15 IL IL60599A patent/IL60599A0/xx unknown
- 1980-07-15 IL IL60598A patent/IL60598A0/xx unknown

Also Published As

Publication number	Publication date
JPS5373548A (en)	1978-06-30
SE7714110L (sv)	1978-06-15
NO774285L (no)	1978-06-15
GB1584298A (en)	1981-02-11
ATA892577A (de)	1979-08-15
IE46013B1 (en)	1983-01-26
AU515268B2 (en)	1981-03-26
DK144640B (da)	1982-04-26
DE2753315A1 (de)	1978-06-15
ES465056A2 (es)	1979-01-16
DK144640C (da)	1982-10-04
SU799646A3 (ru)	1981-01-23
BE861826R (fr)	1978-06-14
IL60599A0 (en)	1980-09-16
MX4954E (es)	1983-01-13
CA1088554A (fr)	1980-10-28
AU3153077A (en)	1979-06-21
IE46013L (en)	1978-06-14
SE436740B (sv)	1985-01-21
CH627728A5 (en)	1982-01-29
FR2374032A2 (fr)	1978-07-13
AT355559B (de)	1980-03-10
NL7713876A (nl)	1978-06-16
FR2374032B2 (de)	1979-03-30
ZA777438B (en)	1979-05-30
DK554677A (da)	1978-06-15
IL60598A0 (en)	1980-09-16
DD133323A6 (de)	1978-12-27

Publication	Publication Date	Title
US4110337A (en)	1978-08-29	Triazolobenzodiazepines
US4277497A (en)	1981-07-07	Analgesic 2-(M-benzoylphenoxy)-propionic acid derivatives
Goel et al.	1999	2-Substituted-3-(4-bromo-2-carboxyphenyl)-5-methyl-4-thiazolidinones as potential anti-inflammatory agents
US3784701A (en)	1974-01-08	Compositions containing substituted benzoylpropionic acids and method of use to treat inflammation and pain
US3349088A (en)	1967-10-24	Therapeutically valuable 1, 2-dihyro-1, 2, 4-benzotriazine derivatives and process for preparation thereof
HU179746B (en)	1982-12-28	Process for producing new spiro-oxasolidines
US4111962A (en)	1978-09-05	Certain substituted 2-phenylnaphtho[1,2-b]furane and -[2,1-b]furane
US4011328A (en)	1977-03-08	Derivatives of pyridine-3-acetic acid, process for their preparation and applications thereof
JPH035455A (ja)	1991-01-11	置換ピロリジン化合物および医薬組成物
JPH0215048A (ja)	1990-01-18	ネオペンチルエステル誘導体、その製造法およびその医薬としての使用
US3255242A (en)	1966-06-07	(alpha-alkylideneacyl)naphthyloxy monocarboxylic acids
HU177226B (en)	1981-08-28	Process for preparing 5-/substituted/-2-indane-carboxylic acid derivatives
US3966783A (en)	1976-06-29	Compounds
US4116972A (en)	1978-09-26	Anti-inflammatory 1-oxo-isoindoline derivatives and processes for their preparation
US3872108A (en)	1975-03-18	Novel chromone derivatives and the production thereof
US4362891A (en)	1982-12-07	Alkanoic acid derivatives
US3984534A (en)	1976-10-05	Tetrazolyl anthraquinones for inhibiting the release of spasmogen mediators
SU1591808A3 (ru)	1990-09-07	Способ получения замещенных 3-фенил-7н-тиазпло[3,2-ъ] [1,2,4]'· триазин-7-онов и способ получения 2-амино-6н-1,3,4-тиадиазинов
US4269848A (en)	1981-05-26	5-Substituted indan-2-carboxylic acid and functional derivatives
GB2023599A (en)	1980-01-03	Furopyridone derivatives
US4097582A (en)	1978-06-27	6',2-(2'-Arylchromonyl) propionic acids, and analgesic and anti-inflammatory derivatives thereof
JPS6033373B2 (ja)	1985-08-02	１−ナフチル酢酸誘導体、その製造法ならびに１−ナフチル酢酸誘導体を含有する薬剤
US4122200A (en)	1978-10-24	6',2-(2'Arylchromonyl) propionic acids, and analgesic and anti-inflammatory derivatives thereof
JPS6324498B2 (de)	1988-05-20
US4224341A (en)	1980-09-23	5-Substituted indan-2 carboxylic acid and functional derivatives