GB1335227A - Tetrahydrocarbazole carboxylic acids and esters and preparation thereof - Google Patents
Tetrahydrocarbazole carboxylic acids and esters and preparation thereofInfo
- Publication number
- GB1335227A GB1335227A GB1845971*[A GB1845971A GB1335227A GB 1335227 A GB1335227 A GB 1335227A GB 1845971 A GB1845971 A GB 1845971A GB 1335227 A GB1335227 A GB 1335227A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- alkyl
- reaction
- phenyl
- prepared
- Prior art date
- 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
Links
- QFLIXPBSNSYURJ-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole-1-carboxylic acid Chemical class N1C2=CC=CC=C2C2=C1C(C(=O)O)CCC2 QFLIXPBSNSYURJ-UHFFFAOYSA-N 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 17
- -1 phenoxy, phenyl Chemical group 0.000 abstract 13
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 238000006243 chemical reaction Methods 0.000 abstract 12
- 125000003545 alkoxy group Chemical group 0.000 abstract 8
- 125000001475 halogen functional group Chemical group 0.000 abstract 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 3
- 125000004953 trihalomethyl group Chemical group 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 150000003839 salts Chemical group 0.000 abstract 2
- ZWMQVBSLMQSMDH-UHFFFAOYSA-N (2-bromophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Br ZWMQVBSLMQSMDH-UHFFFAOYSA-N 0.000 abstract 1
- PVRSIFAEUCUJPK-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine Chemical compound COC1=CC=C(NN)C=C1 PVRSIFAEUCUJPK-UHFFFAOYSA-N 0.000 abstract 1
- HYWSVKNURKQBPT-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole-4-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1CCCC2C(=O)O HYWSVKNURKQBPT-UHFFFAOYSA-N 0.000 abstract 1
- NHOAIPRHGSAFDL-UHFFFAOYSA-N 4-oxocyclohexane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC(=O)CC1 NHOAIPRHGSAFDL-UHFFFAOYSA-N 0.000 abstract 1
- ZFFCJKFLRDPDPL-UHFFFAOYSA-N 6-methoxy-2,3,4,9-tetrahydro-1h-carbazole-4-carboxylic acid Chemical compound C1CCC(C(O)=O)C2=C1NC1=CC=C(OC)C=C12 ZFFCJKFLRDPDPL-UHFFFAOYSA-N 0.000 abstract 1
- YRLYQDDNJQFRQR-UHFFFAOYSA-N 9-[(4-chlorophenyl)methyl]-6-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid Chemical compound C1=2CCCC(C(O)=O)C=2C2=CC(OC)=CC=C2N1CC1=CC=C(Cl)C=C1 YRLYQDDNJQFRQR-UHFFFAOYSA-N 0.000 abstract 1
- MMVMNZMLPWLVPF-UHFFFAOYSA-N 9-benzyl-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid Chemical compound OC(=O)C1CCCC2=C1C1=CC=CC=C1N2CC1=CC=CC=C1 MMVMNZMLPWLVPF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- FGSGHBPKHFDJOP-UHFFFAOYSA-N ethyl 2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCCC1=O FGSGHBPKHFDJOP-UHFFFAOYSA-N 0.000 abstract 1
- VKCMWLOBUILIOQ-UHFFFAOYSA-N ethyl 3-bromo-2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCC(Br)C1=O VKCMWLOBUILIOQ-UHFFFAOYSA-N 0.000 abstract 1
- KMDYKNFDZQVQAY-UHFFFAOYSA-N ethyl 3-bromocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCC(Br)C1 KMDYKNFDZQVQAY-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- ISRLHWRJFFDJQH-UHFFFAOYSA-N n-(2-bromophenyl)-n-(ethylideneamino)benzamide Chemical compound C=1C=CC=C(Br)C=1N(N=CC)C(=O)C1=CC=CC=C1 ISRLHWRJFFDJQH-UHFFFAOYSA-N 0.000 abstract 1
- ILWSAUNMQFNDPO-UHFFFAOYSA-N n-(benzylideneamino)-4-methoxyaniline Chemical compound C1=CC(OC)=CC=C1NN=CC1=CC=CC=C1 ILWSAUNMQFNDPO-UHFFFAOYSA-N 0.000 abstract 1
- UBAYOEQOPWECKF-UHFFFAOYSA-N n-(benzylideneamino)-n-(2-fluorophenyl)benzamide Chemical compound FC1=CC=CC=C1N(C(=O)C=1C=CC=CC=1)N=CC1=CC=CC=C1 UBAYOEQOPWECKF-UHFFFAOYSA-N 0.000 abstract 1
- LKJREFMWHBWKNF-UHFFFAOYSA-N n-(benzylideneamino)-n-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1N(C(=O)C=1C=CC=CC=1)N=CC1=CC=CC=C1 LKJREFMWHBWKNF-UHFFFAOYSA-N 0.000 abstract 1
- LIJJGMDKVVOEFT-UHFFFAOYSA-N n-benzyl-4-methoxyaniline Chemical compound C1=CC(OC)=CC=C1NCC1=CC=CC=C1 LIJJGMDKVVOEFT-UHFFFAOYSA-N 0.000 abstract 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 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
- C07D317/72—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 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4262070A | 1970-06-02 | 1970-06-02 | |
| US20020571A | 1971-11-18 | 1971-11-18 | |
| US314099A US3905998A (en) | 1970-06-02 | 1972-12-11 | 1,2,3,4 Tetrahydrocarbazole-3-carboxylic and 4-carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1335227A true GB1335227A (en) | 1973-10-24 |
Family
ID=27366172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1845971*[A Expired GB1335227A (en) | 1970-06-02 | 1971-06-01 | Tetrahydrocarbazole carboxylic acids and esters and preparation thereof |
Country Status (8)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4060550A (en) * | 1970-08-26 | 1977-11-29 | Sumitomo Chemical Company, Limited | Novel n'-acylated phenyl-hydrazine and -hydrazone derivatives |
| US3941805A (en) * | 1972-11-17 | 1976-03-02 | Sterling Drug Inc. | 3-Halomethylcarbonyl-9-benzoyl-1,2,3,4-tetrahydrocarbazoles |
| US3835152A (en) * | 1972-11-17 | 1974-09-10 | Sterling Drug Inc | 3-cyano-9-benzoyl-1,2,3,4-tetrahydro carbazole |
| US3948938A (en) * | 1972-12-29 | 1976-04-06 | American Color & Chemical Corporation | Polymeric materials colored with yellow methine dyes and pigments |
| ATE90076T1 (de) | 1986-03-27 | 1993-06-15 | Merck Frosst Canada Inc | Tetrahydrocarbazole ester. |
| US4775680A (en) * | 1987-07-21 | 1988-10-04 | Merck & Co., Inc. | Cyclohept[b]indolealkanoic acids, pharmaceutical compositions and use |
| CA2196046A1 (en) * | 1994-07-27 | 1996-02-08 | Nigel Birdsall | Heterocyclic compounds, useful as allosteric effectors at muscarinic receptors |
| PT1833791E (pt) * | 2004-12-27 | 2011-10-19 | Actelion Pharmaceuticals Ltd | Derivados de 2,3,4,9-tetra-hidro-1h-carbazol como antgonistas do receptor crth2 |
| US7662831B2 (en) * | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
| US7601856B2 (en) * | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| US9346803B2 (en) | 2011-10-17 | 2016-05-24 | Vanderbilt University | Indomethacin analogs for the treatment of castrate-resistant prostate cancer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1915334A (en) * | 1930-10-16 | 1933-06-27 | Du Pont | Fluosilicate of organic heterocyclic bases and process of making it |
| US2075359A (en) * | 1930-10-16 | 1937-03-30 | Du Pont | Insecticide |
-
1970
- 1970-06-02 US US42620A patent/US3687969A/en not_active Expired - Lifetime
-
1971
- 1971-05-28 CA CA114,287A patent/CA960665A/en not_active Expired
- 1971-06-01 GB GB1845971*[A patent/GB1335227A/en not_active Expired
- 1971-06-02 CH CH800471A patent/CH533112A/fr not_active IP Right Cessation
- 1971-06-02 BE BE767968A patent/BE767968A/xx unknown
- 1971-06-02 NL NL7107589A patent/NL7107589A/xx not_active Application Discontinuation
- 1971-06-02 FR FR7119972A patent/FR2100715B1/fr not_active Expired
- 1971-06-02 DE DE19712127352 patent/DE2127352A1/de not_active Ceased
- 1971-11-18 US US00200205A patent/US3758496A/en not_active Expired - Lifetime
-
1972
- 1972-12-11 US US314099A patent/US3905998A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL7107589A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-12-06 |
| FR2100715B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-08-23 |
| BE767968A (fr) | 1971-12-02 |
| DE2127352A1 (de) | 1972-01-27 |
| US3905998A (en) | 1975-09-16 |
| FR2100715A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-03-24 |
| CA960665A (en) | 1975-01-07 |
| US3758496A (en) | 1973-09-11 |
| US3687969A (en) | 1972-08-29 |
| CH533112A (fr) | 1973-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |