CA1088554A - Preparation de l'acide indane-2 carboxylique substitue en position 5 et ses derives - Google Patents

Preparation de l'acide indane-2 carboxylique substitue en position 5 et ses derives

Info

Publication number: CA1088554A
Authority: CA; Canada
Prior art keywords: indane; radical; acid; benzoyl; formula
Prior art date: 1976-12-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA293,076A

Other languages

English (en)

French (fr)

Inventor

Michel Bayssat

Francis Sautel

Jean-Claude Depin

Annie Betbeder-Matibet

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

Merck Sante SAS

Original Assignee

LIPHA Liyonnaise Industrielle Pharmaceutique

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

1977-12-14

Publication date

1980-10-28

1977-12-14 Application filed by LIPHA Liyonnaise Industrielle Pharmaceutique filed Critical LIPHA Liyonnaise Industrielle Pharmaceutique

1980-10-28 Application granted granted Critical

1980-10-28 Publication of CA1088554A publication Critical patent/CA1088554A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 13
-1 5-substituted indane-2 carboxylic acid Chemical class 0.000 title claims description 35
150000001875 compounds Chemical class 0.000 claims abstract description 35
229910052736 halogen Inorganic materials 0.000 claims abstract description 19
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 18
150000002367 halogens Chemical class 0.000 claims abstract description 17
125000001424 substituent group Chemical group 0.000 claims abstract description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 3
125000004663 dialkyl amino group Chemical group 0.000 claims abstract 3
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims abstract 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 46
239000002253 acid Substances 0.000 claims description 45
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 44
XUDCMQBOWOLYCF-UHFFFAOYSA-N 2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)CC2=C1 XUDCMQBOWOLYCF-UHFFFAOYSA-N 0.000 claims description 37
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 27
230000008569 process Effects 0.000 claims description 25
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 19
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 13
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 11
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
150000003857 carboxamides Chemical class 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
238000010992 reflux Methods 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
LDUHQKWPUVJJPU-UHFFFAOYSA-N 2,3-dihydro-1h-indene-2-carboxamide Chemical compound C1=CC=C2CC(C(=O)N)CC2=C1 LDUHQKWPUVJJPU-UHFFFAOYSA-N 0.000 claims description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
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 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 7
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 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000004103 aminoalkyl group Chemical group 0.000 claims description 6
150000002468 indanes Chemical class 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
QDLFVXRWLQSBTF-UHFFFAOYSA-N 1,1,2-triethylhydrazine Chemical compound CCNN(CC)CC QDLFVXRWLQSBTF-UHFFFAOYSA-N 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
150000001735 carboxylic acids Chemical class 0.000 claims description 4
238000006193 diazotization reaction Methods 0.000 claims description 4
150000001350 alkyl halides Chemical class 0.000 claims description 3
150000007942 carboxylates Chemical class 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
150000001879 copper Chemical class 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 2
239000000126 substance Substances 0.000 claims 19
MCMQEARTOUMJPK-UHFFFAOYSA-N 2,3-dihydro-1h-indene;propanoic acid Chemical compound CCC(O)=O.C1=CC=C2CCCC2=C1 MCMQEARTOUMJPK-UHFFFAOYSA-N 0.000 claims 2
JTTVFOGHBRSFQM-UHFFFAOYSA-N C(C)NCC.ClCCCl Chemical compound C(C)NCC.ClCCCl JTTVFOGHBRSFQM-UHFFFAOYSA-N 0.000 claims 2
230000001476 alcoholic effect Effects 0.000 claims 2
150000001768 cations Chemical class 0.000 claims 2
230000007062 hydrolysis Effects 0.000 claims 2
238000006460 hydrolysis reaction Methods 0.000 claims 2
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 claims 1
DZGMFITYAJIDHR-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)CCC2=C1 DZGMFITYAJIDHR-UHFFFAOYSA-N 0.000 claims 1
AJSVPEVDFBYRCH-UHFFFAOYSA-N 3-methylthiophene-2-carbonyl chloride Chemical compound CC=1C=CSC=1C(Cl)=O AJSVPEVDFBYRCH-UHFFFAOYSA-N 0.000 claims 1
OVOCLWJUABOAPL-UHFFFAOYSA-N 5-methylfuran-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)O1 OVOCLWJUABOAPL-UHFFFAOYSA-N 0.000 claims 1
YDUOFRZUFBNVOO-UHFFFAOYSA-N 6-sulfonylcyclohexa-2,4-diene-1-carbonyl chloride Chemical compound S(=O)(=O)=C1C(C(=O)Cl)C=CC=C1 YDUOFRZUFBNVOO-UHFFFAOYSA-N 0.000 claims 1
241001331845 Equus asinus x caballus Species 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
230000001760 anti-analgesic effect Effects 0.000 abstract description 2
230000000702 anti-platelet effect Effects 0.000 abstract description 2
239000003146 anticoagulant agent Substances 0.000 abstract description 2
231100000926 not very toxic Toxicity 0.000 abstract description 2
230000000144 pharmacologic effect Effects 0.000 abstract description 2
239000008194 pharmaceutical composition Substances 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
239000000203 mixture Substances 0.000 description 16
239000007787 solid Substances 0.000 description 16
238000002329 infrared spectrum Methods 0.000 description 15
239000000243 solution Substances 0.000 description 14
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000001953 recrystallisation Methods 0.000 description 12
230000008018 melting Effects 0.000 description 11
238000002844 melting Methods 0.000 description 11
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
239000012141 concentrate Substances 0.000 description 10
150000003254 radicals Chemical group 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000047 product Substances 0.000 description 8
239000000706 filtrate Substances 0.000 description 7
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
238000013019 agitation Methods 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
229940039748 oxalate Drugs 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
230000007704 transition Effects 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
238000003756 stirring Methods 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
102000008186 Collagen Human genes 0.000 description 3
108010035532 Collagen Proteins 0.000 description 3
101100020663 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppm-1 gene Proteins 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
229920001436 collagen Polymers 0.000 description 3
239000005457 ice water Substances 0.000 description 3
229940072033 potash Drugs 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
238000007792 addition Methods 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
238000004220 aggregation Methods 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
230000002744 anti-aggregatory effect Effects 0.000 description 2
239000008346 aqueous phase Substances 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
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000000679 carrageenan Substances 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
229940113118 carrageenan Drugs 0.000 description 2
239000002826 coolant Substances 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000012071 phase Substances 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
239000002244 precipitate Substances 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
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
235000010269 sulphur dioxide Nutrition 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
RTRZIWZZYGDMFE-UHFFFAOYSA-N 1-chloro-n,n-diethylethanamine;hydron;chloride Chemical compound Cl.CCN(CC)C(C)Cl RTRZIWZZYGDMFE-UHFFFAOYSA-N 0.000 description 1
KTUOJDXAHZOFCA-UHFFFAOYSA-N 3-(diethylamino)propanamide Chemical compound CCN(CC)CCC(N)=O KTUOJDXAHZOFCA-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241001338801 Chlorus Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
206010015150 Erythema Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
206010061218 Inflammation Diseases 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
229920002472 Starch Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
BUVKILSTJGGJJN-UHFFFAOYSA-N acetic acid;2,3-dihydro-1h-indene Chemical compound CC(O)=O.C1=CC=C2CCCC2=C1 BUVKILSTJGGJJN-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
230000007423 decrease Effects 0.000 description 1
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
239000000539 dimer Substances 0.000 description 1
125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
231100000321 erythema Toxicity 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000036541 health Effects 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000004054 inflammatory process Effects 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
150000002500 ions Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000011068 loading method Methods 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
239000000155 melt Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000003507 refrigerant Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
229940100445 wheat starch Drugs 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)
Neurology (AREA)
Diabetes (AREA)
Biomedical Technology (AREA)
Hematology (AREA)
Neurosurgery (AREA)
Rheumatology (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)

CA293,076A 1976-12-14 1977-12-14 Preparation de l'acide indane-2 carboxylique substitue en position 5 et ses derives Expired CA1088554A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7637574A FR2374032A2 (fr)	1976-12-14	1976-12-14	Nouveaux acides carboxyliques derives de l'indane
FR76.37754		1976-12-14

Publications (1)

Publication Number	Publication Date
CA1088554A true CA1088554A (fr)	1980-10-28

Family

ID=9181028

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA293,076A Expired CA1088554A (fr)	1976-12-14	1977-12-14	Preparation de l'acide indane-2 carboxylique substitue en position 5 et ses derives

Country Status (21)

Country	Link
JP (1)	JPS5373548A (da)
AT (1)	AT355559B (da)
AU (1)	AU515268B2 (da)
BE (1)	BE861826R (da)
CA (1)	CA1088554A (da)
CH (1)	CH627728A5 (da)
DD (1)	DD133323A6 (da)
DE (1)	DE2753315A1 (da)
DK (1)	DK144640C (da)
ES (1)	ES465056A2 (da)
FR (1)	FR2374032A2 (da)
GB (1)	GB1584298A (da)
HU (1)	HU177226B (da)
IE (1)	IE46013B1 (da)
IL (2)	IL60598A0 (da)
MX (1)	MX4954E (da)
NL (1)	NL7713876A (da)
NO (1)	NO774285L (da)
SE (1)	SE436740B (da)
SU (1)	SU799646A3 (da)
ZA (1)	ZA777438B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2526124T3 (es) *	2010-06-16	2015-01-07	Cymabay Therapeutics, Inc.	Agonistas del receptor GPR120 y sus usos

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4980053A (da) *	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 (da) *	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 NO NO774285A patent/NO774285L/no unknown
- 1977-12-13 HU HU77LI316A patent/HU177226B/hu unknown
- 1977-12-13 SE SE7714110A patent/SE436740B/sv unknown
- 1977-12-13 DK DK554677A patent/DK144640C/da not_active IP Right Cessation
- 1977-12-13 MX MX776686U patent/MX4954E/es unknown
- 1977-12-13 DD DD7700202588A patent/DD133323A6/xx unknown
- 1977-12-13 IE IE2520/77A patent/IE46013B1/en unknown
- 1977-12-14 NL NL7713876A patent/NL7713876A/xx not_active Application Discontinuation
- 1977-12-14 AU AU31530/77A patent/AU515268B2/en not_active Expired
- 1977-12-14 ES ES465056A patent/ES465056A2/es not_active Expired
- 1977-12-14 JP JP14943377A patent/JPS5373548A/ja active Pending
- 1977-12-14 AT AT892577A patent/AT355559B/de not_active IP Right Cessation
- 1977-12-14 BE BE183429A patent/BE861826R/xx not_active IP Right Cessation
- 1977-12-14 CA CA293,076A patent/CA1088554A/fr not_active Expired
- 1977-12-14 CH CH1541077A patent/CH627728A5/fr not_active IP Right Cessation
- 1977-12-14 ZA ZA00777438A patent/ZA777438B/xx unknown
1979
- 1979-04-06 SU SU792746906A patent/SU799646A3/ru active
1980
- 1980-07-15 IL IL60598A patent/IL60598A0/xx unknown
- 1980-07-15 IL IL60599A patent/IL60599A0/xx unknown

Also Published As

Publication number	Publication date
MX4954E (es)	1983-01-13
AU3153077A (en)	1979-06-21
DK144640B (da)	1982-04-26
JPS5373548A (en)	1978-06-30
DD133323A6 (de)	1978-12-27
ES465056A2 (es)	1979-01-16
DK554677A (da)	1978-06-15
SU799646A3 (ru)	1981-01-23
IL60599A0 (en)	1980-09-16
IE46013B1 (en)	1983-01-26
GB1584298A (en)	1981-02-11
NO774285L (no)	1978-06-15
CH627728A5 (en)	1982-01-29
DK144640C (da)	1982-10-04
AU515268B2 (en)	1981-03-26
SE436740B (sv)	1985-01-21
IE46013L (en)	1978-06-14
NL7713876A (nl)	1978-06-16
BE861826R (fr)	1978-06-14
FR2374032B2 (da)	1979-03-30
DE2753315A1 (de)	1978-06-15
AT355559B (de)	1980-03-10
ATA892577A (de)	1979-08-15
IL60598A0 (en)	1980-09-16
SE7714110L (sv)	1978-06-15
ZA777438B (en)	1979-05-30
FR2374032A2 (fr)	1978-07-13
HU177226B (en)	1981-08-28

Legal Events

Date	Code	Title	Description
1997-10-28	MKEX	Expiry

Publication	Publication Date	Title
JPS5811850B2 (ja)	1983-03-04	１− オキソ −２，２− ジチカン −５− インダニロキシ（マタハチオ＃アルカノイツクアシド
US3766259A (en)	1973-10-16	Preparation of 1-aryl-3-indenyl acetic acids
CH641798A5 (fr)	1984-03-15	Derives de dibenzothiepinne et leur procede de synthese.
Blicke et al.	1930	Local Anesthetics in the Pyrrole Series. I1, 2
Kipnis et al.	1949	2-Acyloxyacetylthiophenes
DE2740836A1 (de)	1979-03-22	Anellierte indolderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
Cass	1942	2-Phenyloxazole and ortho-substituted derivatives
US3663627A (en)	1972-05-16	1-indanmethanols
EP0064445A1 (fr)	1982-11-10	Dialcoxy (2,4) benzènesulfonamides N-substitués
CH615414A5 (da)	1980-01-31
CH622795A5 (da)	1981-04-30
CA1249834A (fr)	1989-02-07	Preparation d'acides dihydro-5,6-4h-cyclopenta ¬b\|thiophenecarboxyliques-6
EP0064006B1 (fr)	1984-10-31	Chlorures de dialcoxy (2,4) benzènesulfonyle substitués
DE1593091C3 (da)	1974-01-03
US2993891A (en)	1961-07-25	Butyrolactone derivatives
US3598867A (en)	1971-08-10	Dibenzocyclohepta-triene and-diene derivatives
FR2478640A1 (fr)	1981-09-25	Nouvelles thieno (2,3-d) pyridazinones-4 et thieno (2,3-d) pyridazinones-7, leur procede de preparation et leur therapeutique
KR870000034B1 (ko)	1987-02-07	〔1-옥소-2-아릴 또는 티에닐-2-치환-5-인다닐옥시〕알칸산의 제조방법
CH627728A5 (en)	1982-01-29	Preparation of carboxylic acids derived from indane
Hale et al.	1913	Studies in the Cyclopentadiene Series. III. Certain Derivatives of 2, 3-DIBENZOYL-5-NITROCYCLO-PENTADIENE.
LU86706A1 (fr)	1987-07-24	Nouveaux derives du benzo(4,5)cyclohepta(1,2-b)thiophene,leur preparation et leur utilisation comme medicaments
US3322821A (en)	1967-05-30	Process for converting [4-[2-(organosulfinylmethyl)alkanoyl]phenoxy]alkanoic acids and [4-[2-(organosulfonylmethyl)alkanoyl]phenoxy]alkanoic acids to their [4-(2-methylenealkanoyl)phenoxy]alkanoic acid derivatives
US3275689A (en)	1966-09-27	3-alkylsulfonyl-5-(tertiaryaminopropylidene)-and 5-hydroxy-5-(tertiaryaminopropyl)-5h-dibenzo[a, d] cycloheptenes
US3337623A (en)	1967-08-22	Cyanamide derivatives of tetrahydrodibenzo[a, d]cyclooctene
CH617173A5 (da)	1980-05-14