NO783589L - Analogifremgangsmaate for fremstilling av nye derivater av dibenzo(a,d)cyklohepten - Google Patents
Analogifremgangsmaate for fremstilling av nye derivater av dibenzo(a,d)cykloheptenInfo
- Publication number
- NO783589L NO783589L NO78783589A NO783589A NO783589L NO 783589 L NO783589 L NO 783589L NO 78783589 A NO78783589 A NO 78783589A NO 783589 A NO783589 A NO 783589A NO 783589 L NO783589 L NO 783589L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- cyclohepten
- preparation
- acid
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical class C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- USROOJDCPHEUKV-UHFFFAOYSA-N 2-[2-[3-(cyanomethyl)phenyl]ethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC(CC#N)=C1 USROOJDCPHEUKV-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- CFSGLZBKKOCSIC-UHFFFAOYSA-N 2-(11-oxo-5,6-dihydrodibenzo[2,1-b:3',1'-f][7]annulen-3-yl)acetamide Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=C(CC(=O)N)C=C12 CFSGLZBKKOCSIC-UHFFFAOYSA-N 0.000 description 3
- BMAKGEIWNQPUJT-UHFFFAOYSA-N 2-[2-[3-(1-cyanoethyl)phenyl]ethyl]benzoic acid Chemical compound N#CC(C)C1=CC=CC(CCC=2C(=CC=CC=2)C(O)=O)=C1 BMAKGEIWNQPUJT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- HMFNAOVIFKUVFI-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)ethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=C(Cl)C=C1 HMFNAOVIFKUVFI-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241000700159 Rattus Species 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OYUDOANJBAWBBO-UHFFFAOYSA-N 2-(11-oxo-5,6-dihydrodibenzo[2,1-b:3',1'-f][7]annulen-3-yl)acetic acid Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=C(CC(=O)O)C=C12 OYUDOANJBAWBBO-UHFFFAOYSA-N 0.000 description 1
- AYNKNYOOGBRSMS-UHFFFAOYSA-N 2-(11-oxo-5,6-dihydrodibenzo[2,1-b:3',1'-f][7]annulen-3-yl)butanamide Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=C(C(C(N)=O)CC)C=C12 AYNKNYOOGBRSMS-UHFFFAOYSA-N 0.000 description 1
- MRZPOBQLAMVEKI-UHFFFAOYSA-N 2-(11-oxo-5,6-dihydrodibenzo[2,1-b:3',1'-f][7]annulen-3-yl)butanoic acid Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=C(C(C(O)=O)CC)C=C12 MRZPOBQLAMVEKI-UHFFFAOYSA-N 0.000 description 1
- ZWXOXXIZUXWWCG-UHFFFAOYSA-N 2-(11-oxo-5,6-dihydrodibenzo[2,1-b:3',1'-f][7]annulen-3-yl)propanamide Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=C(C(C(N)=O)C)C=C12 ZWXOXXIZUXWWCG-UHFFFAOYSA-N 0.000 description 1
- MYABOUMUQWTSTR-UHFFFAOYSA-N 2-(11-oxo-5,6-dihydrodibenzo[2,1-b:3',1'-f][7]annulen-3-yl)propanoic acid Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=C(C(C(O)=O)C)C=C12 MYABOUMUQWTSTR-UHFFFAOYSA-N 0.000 description 1
- DWXSYDKEWORWBT-UHFFFAOYSA-N 2-(2-bromophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1Br DWXSYDKEWORWBT-UHFFFAOYSA-N 0.000 description 1
- IUJAAIZKRJJZGQ-UHFFFAOYSA-N 2-(2-chlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1Cl IUJAAIZKRJJZGQ-UHFFFAOYSA-N 0.000 description 1
- ALXADGDGMRJAGC-UHFFFAOYSA-N 2-(2-oxo-5-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)propanoic acid Chemical compound O=C1C2=C(CCC3=C1C=C(C=C3)C(C(=O)O)C)C=CC=C2 ALXADGDGMRJAGC-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- -1 2-(5-oxo-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)-pentanoic acid Chemical compound 0.000 description 1
- JUJWMNSZEZGSCY-UHFFFAOYSA-N 2-[2-[4-(cyanomethyl)phenyl]ethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=C(CC#N)C=C1 JUJWMNSZEZGSCY-UHFFFAOYSA-N 0.000 description 1
- QOWSWEBLNVACCL-UHFFFAOYSA-N 4-Bromophenyl acetate Chemical compound OC(=O)CC1=CC=C(Br)C=C1 QOWSWEBLNVACCL-UHFFFAOYSA-N 0.000 description 1
- CDPKJZJVTHSESZ-UHFFFAOYSA-N 4-chlorophenylacetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C=C1 CDPKJZJVTHSESZ-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000008508 dibenzocycloheptenes Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/86—Unsaturated compounds containing keto groups containing six-membered aromatic rings and other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7307508A FR2219777A1 (en) | 1973-03-02 | 1973-03-02 | 5-oxo dibenzo(a,d)cycloheptene derivs - with analgesic, antipyretic and anti-inflamm- atory activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO783589L true NO783589L (no) | 1974-09-03 |
Family
ID=9115696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO78783589A NO783589L (no) | 1973-03-02 | 1978-10-24 | Analogifremgangsmaate for fremstilling av nye derivater av dibenzo(a,d)cyklohepten |
Country Status (12)
| Country | Link |
|---|---|
| AR (1) | AR202847A1 (cs) |
| BE (1) | BE811794A (cs) |
| CH (1) | CH589033A5 (cs) |
| CS (1) | CS188196B2 (cs) |
| ES (1) | ES425405A1 (cs) |
| FR (1) | FR2219777A1 (cs) |
| HU (1) | HU168680B (cs) |
| NO (1) | NO783589L (cs) |
| PL (1) | PL97904B1 (cs) |
| SE (1) | SE413138B (cs) |
| SU (1) | SU564804A3 (cs) |
| ZA (1) | ZA741327B (cs) |
-
1973
- 1973-03-02 FR FR7307508A patent/FR2219777A1/fr active Granted
-
1974
- 1974-02-28 CS CS763032A patent/CS188196B2/cs unknown
- 1974-02-28 ZA ZA00741327A patent/ZA741327B/xx unknown
- 1974-03-01 CH CH53277A patent/CH589033A5/xx not_active IP Right Cessation
- 1974-03-01 HU HURO827A patent/HU168680B/hu unknown
- 1974-03-01 BE BE141578A patent/BE811794A/xx unknown
- 1974-03-02 PL PL1974188427A patent/PL97904B1/pl unknown
- 1974-04-17 ES ES425405A patent/ES425405A1/es not_active Expired
- 1974-10-15 AR AR256101A patent/AR202847A1/es active
-
1975
- 1975-06-05 SU SU7502140475A patent/SU564804A3/ru active
-
1976
- 1976-10-13 SE SE7611369A patent/SE413138B/xx unknown
-
1978
- 1978-10-24 NO NO78783589A patent/NO783589L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS188196B2 (en) | 1979-02-28 |
| HU168680B (cs) | 1976-06-28 |
| ES425405A1 (es) | 1976-05-16 |
| ZA741327B (en) | 1975-02-26 |
| FR2219777A1 (en) | 1974-09-27 |
| FR2219777B1 (cs) | 1976-07-16 |
| SE413138B (sv) | 1980-04-21 |
| SE7611369L (sv) | 1976-10-13 |
| SU564804A3 (ru) | 1977-07-05 |
| AR202847A1 (es) | 1975-07-24 |
| CH589033A5 (cs) | 1977-06-30 |
| BE811794A (fr) | 1974-09-02 |
| PL97904B1 (pl) | 1978-03-30 |
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