JP2007501284A5 - - Google Patents
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- JP2007501284A5 JP2007501284A5 JP2006533561A JP2006533561A JP2007501284A5 JP 2007501284 A5 JP2007501284 A5 JP 2007501284A5 JP 2006533561 A JP2006533561 A JP 2006533561A JP 2006533561 A JP2006533561 A JP 2006533561A JP 2007501284 A5 JP2007501284 A5 JP 2007501284A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- carbazol
- amine
- bromo
- compound according
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 208000009608 Papillomavirus Infections Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 3
- 150000001540 azides Chemical class 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- ZOFYAVWOFRSXCF-UHFFFAOYSA-N 2-bromo-n-pyrimidin-2-yl-5,6,7,8,9,10-hexahydrocyclohepta[b]indol-6-amine Chemical compound C1CCCC=2C3=CC(Br)=CC=C3NC=2C1NC1=NC=CC=N1 ZOFYAVWOFRSXCF-UHFFFAOYSA-N 0.000 claims 2
- BVOFUWLUTQYKDG-UHFFFAOYSA-N 6-[(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)amino]pyridine-3-carbonitrile Chemical compound C1CCC=2C3=CC(Br)=CC=C3NC=2C1NC1=CC=C(C#N)C=N1 BVOFUWLUTQYKDG-UHFFFAOYSA-N 0.000 claims 2
- UYVGHBBQELYFCQ-UHFFFAOYSA-N 6-[(6-methyl-2,3,4,9-tetrahydro-1h-carbazol-1-yl)amino]pyridine-3-carbonitrile;hydrochloride Chemical compound Cl.C1CCC=2C3=CC(C)=CC=C3NC=2C1NC1=CC=C(C#N)C=N1 UYVGHBBQELYFCQ-UHFFFAOYSA-N 0.000 claims 2
- QODCQNSYEPOBKP-UHFFFAOYSA-N 6-bromo-9-(4-fluorophenoxy)-1,2,3,4-tetrahydrocarbazole Chemical compound C1=CC(F)=CC=C1ON1C2=CC=C(Br)C=C2C2=C1CCCC2 QODCQNSYEPOBKP-UHFFFAOYSA-N 0.000 claims 2
- NPSWQSOJFITSQW-UHFFFAOYSA-N 6-bromo-n-(2-chlorophenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound ClC1=CC=CC=C1NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 NPSWQSOJFITSQW-UHFFFAOYSA-N 0.000 claims 2
- SEJSBJDWWVNEOP-UHFFFAOYSA-N 6-bromo-n-(2-fluorophenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound FC1=CC=CC=C1NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 SEJSBJDWWVNEOP-UHFFFAOYSA-N 0.000 claims 2
- DAWGFSYWAIBWDF-UHFFFAOYSA-N 6-bromo-n-(2-methoxyphenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound COC1=CC=CC=C1NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 DAWGFSYWAIBWDF-UHFFFAOYSA-N 0.000 claims 2
- RNFKEPRDXOGLDK-UHFFFAOYSA-N 6-bromo-n-(3,4-dichlorophenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 RNFKEPRDXOGLDK-UHFFFAOYSA-N 0.000 claims 2
- NNQBFVSAJHLPMW-UHFFFAOYSA-N 6-bromo-n-(3-fluorophenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound FC1=CC=CC(NC2C3=C(C4=CC(Br)=CC=C4N3)CCC2)=C1 NNQBFVSAJHLPMW-UHFFFAOYSA-N 0.000 claims 2
- AFVSFXSRQMVFOT-UHFFFAOYSA-N 6-bromo-n-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound COC1=CC=CC(NC2C3=C(C4=CC(Br)=CC=C4N3)CCC2)=C1 AFVSFXSRQMVFOT-UHFFFAOYSA-N 0.000 claims 2
- VQSLKXMUDAPZRL-UHFFFAOYSA-N 6-bromo-n-(4,6-dimethylpyrimidin-2-yl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine;hydrochloride Chemical compound Cl.CC1=CC(C)=NC(NC2C3=C(C4=CC(Br)=CC=C4N3)CCC2)=N1 VQSLKXMUDAPZRL-UHFFFAOYSA-N 0.000 claims 2
- FQRDSPVFTDFKQY-UHFFFAOYSA-N 6-bromo-n-(4-chlorophenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=CC(Cl)=CC=C1NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 FQRDSPVFTDFKQY-UHFFFAOYSA-N 0.000 claims 2
- FPJATBKJKFZJHN-UHFFFAOYSA-N 6-bromo-n-(4-fluorophenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=CC(F)=CC=C1NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 FPJATBKJKFZJHN-UHFFFAOYSA-N 0.000 claims 2
- GSCHPXDOAXOUSU-UHFFFAOYSA-N 6-bromo-n-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=CC(OC)=CC=C1NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 GSCHPXDOAXOUSU-UHFFFAOYSA-N 0.000 claims 2
- DVOIVRNPXIVKRM-UHFFFAOYSA-N 6-bromo-n-(5-propylpyrimidin-2-yl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound N1=CC(CCC)=CN=C1NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 DVOIVRNPXIVKRM-UHFFFAOYSA-N 0.000 claims 2
- DJQXVPRXEXECEY-UHFFFAOYSA-N 6-bromo-n-[5-(trifluoromethyl)pyridin-2-yl]-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 DJQXVPRXEXECEY-UHFFFAOYSA-N 0.000 claims 2
- HQHNQRXHDAUEGH-UHFFFAOYSA-N 6-bromo-n-[5-(trifluoromethyl)pyrimidin-2-yl]-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound N1=CC(C(F)(F)F)=CN=C1NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 HQHNQRXHDAUEGH-UHFFFAOYSA-N 0.000 claims 2
- IXYPWFUDXMSOQR-UHFFFAOYSA-N 6-bromo-n-phenyl-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1CCC=2C3=CC(Br)=CC=C3NC=2C1NC1=CC=CC=C1 IXYPWFUDXMSOQR-UHFFFAOYSA-N 0.000 claims 2
- BATREXGQQCDBRL-UHFFFAOYSA-N 6-bromo-n-pyridin-2-yl-2,3,4,9-tetrahydro-1h-carbazol-1-amine;hydrochloride Chemical compound Cl.C1CCC=2C3=CC(Br)=CC=C3NC=2C1NC1=CC=CC=N1 BATREXGQQCDBRL-UHFFFAOYSA-N 0.000 claims 2
- XGWDGXXZMLVNDD-UHFFFAOYSA-N 6-bromo-n-pyrimidin-2-yl-2,3,4,9-tetrahydro-1h-carbazol-1-amine;hydrochloride Chemical compound Cl.C1CCC=2C3=CC(Br)=CC=C3NC=2C1NC1=NC=CC=N1 XGWDGXXZMLVNDD-UHFFFAOYSA-N 0.000 claims 2
- VYXAMMHJJFUQRW-UHFFFAOYSA-N 6-chloro-n-(4,6-dimethoxypyrimidin-2-yl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound COC1=CC(OC)=NC(NC2C3=C(C4=CC(Cl)=CC=C4N3)CCC2)=N1 VYXAMMHJJFUQRW-UHFFFAOYSA-N 0.000 claims 2
- QMSCQMGYELSESI-UHFFFAOYSA-N 6-chloro-n-(4,6-dimethylpyrimidin-2-yl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound CC1=CC(C)=NC(NC2C3=C(C4=CC(Cl)=CC=C4N3)CCC2)=N1 QMSCQMGYELSESI-UHFFFAOYSA-N 0.000 claims 2
- JJOPBBXPKCSFNG-UHFFFAOYSA-N 6-chloro-n-(4-chlorophenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=CC(Cl)=CC=C1NC1C(NC=2C3=CC(Cl)=CC=2)=C3CCC1 JJOPBBXPKCSFNG-UHFFFAOYSA-N 0.000 claims 2
- VOOOBNBNHICISG-UHFFFAOYSA-N 6-chloro-n-(4-fluorophenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=CC(F)=CC=C1NC1C(NC=2C3=CC(Cl)=CC=2)=C3CCC1 VOOOBNBNHICISG-UHFFFAOYSA-N 0.000 claims 2
- JJVPUMVFPVRPEK-UHFFFAOYSA-N 6-chloro-n-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=CC(OC)=CC=C1NC1C(NC=2C3=CC(Cl)=CC=2)=C3CCC1 JJVPUMVFPVRPEK-UHFFFAOYSA-N 0.000 claims 2
- NZIDKQYZUMXIPG-UHFFFAOYSA-N 6-chloro-n-(4-methylphenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=CC(C)=CC=C1NC1C(NC=2C3=CC(Cl)=CC=2)=C3CCC1 NZIDKQYZUMXIPG-UHFFFAOYSA-N 0.000 claims 2
- DRYSFMWFBQCPRC-UHFFFAOYSA-N 6-chloro-n-(4-methylpyrimidin-2-yl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound CC1=CC=NC(NC2C3=C(C4=CC(Cl)=CC=C4N3)CCC2)=N1 DRYSFMWFBQCPRC-UHFFFAOYSA-N 0.000 claims 2
- QNTJZKOUHMTCOZ-UHFFFAOYSA-N 6-chloro-n-phenyl-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1CCC=2C3=CC(Cl)=CC=C3NC=2C1NC1=CC=CC=C1 QNTJZKOUHMTCOZ-UHFFFAOYSA-N 0.000 claims 2
- HFXAWOOEADNVFN-UHFFFAOYSA-N 6-chloro-n-pyrimidin-2-yl-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1CCC=2C3=CC(Cl)=CC=C3NC=2C1NC1=NC=CC=N1 HFXAWOOEADNVFN-UHFFFAOYSA-N 0.000 claims 2
- UWIAXQCNDDIQTR-UHFFFAOYSA-N 6-methoxy-n-pyrimidin-2-yl-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1CCC=2C3=CC(OC)=CC=C3NC=2C1NC1=NC=CC=N1 UWIAXQCNDDIQTR-UHFFFAOYSA-N 0.000 claims 2
- YBVVAPJDKGLYGN-UHFFFAOYSA-N 6-methyl-n-pyridin-2-yl-2,3,4,9-tetrahydro-1h-carbazol-1-amine;hydrochloride Chemical compound Cl.C1CCC=2C3=CC(C)=CC=C3NC=2C1NC1=CC=CC=N1 YBVVAPJDKGLYGN-UHFFFAOYSA-N 0.000 claims 2
- 206010059313 Anogenital warts Diseases 0.000 claims 2
- 206010008263 Cervical dysplasia Diseases 0.000 claims 2
- 208000000907 Condylomata Acuminata Diseases 0.000 claims 2
- 241001631646 Papillomaviridae Species 0.000 claims 2
- 241001505332 Polyomavirus sp. Species 0.000 claims 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims 2
- 241000700605 Viruses Species 0.000 claims 2
- 208000000260 Warts Diseases 0.000 claims 2
- 208000025009 anogenital human papillomavirus infection Diseases 0.000 claims 2
- 201000004201 anogenital venereal wart Diseases 0.000 claims 2
- -1 azido compound Chemical class 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 201000010536 head and neck cancer Diseases 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- YJAFEVJACSAADZ-UHFFFAOYSA-N methyl 8-anilino-6,7,8,9-tetrahydro-5h-carbazole-3-carboxylate Chemical compound C1CCC=2C3=CC(C(=O)OC)=CC=C3NC=2C1NC1=CC=CC=C1 YJAFEVJACSAADZ-UHFFFAOYSA-N 0.000 claims 2
- JNRNNQXOROGFHY-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-6-methyl-2,3,4,9-tetrahydro-1h-carbazol-1-amine;hydrochloride Chemical compound Cl.COC1=CC(OC)=NC(NC2C3=C(C4=CC(C)=CC=C4N3)CCC2)=N1 JNRNNQXOROGFHY-UHFFFAOYSA-N 0.000 claims 2
- NACUMKWXHWBWAA-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(NC3C=4NC5=CC=C(C=C5C=4CCC3)Br)=NC2=C1 NACUMKWXHWBWAA-UHFFFAOYSA-N 0.000 claims 2
- KRRAFCHGFZAQOK-UHFFFAOYSA-N n-phenyl-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=2NC3=CC=CC=C3C=2CCCC1NC1=CC=CC=C1 KRRAFCHGFZAQOK-UHFFFAOYSA-N 0.000 claims 2
- FYAPDWQVYMPJNT-UHFFFAOYSA-N n-phenyl-6-(trifluoromethyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine;hydrochloride Chemical compound Cl.C1CCC=2C3=CC(C(F)(F)F)=CC=C3NC=2C1NC1=CC=CC=C1 FYAPDWQVYMPJNT-UHFFFAOYSA-N 0.000 claims 2
- 231100000590 oncogenic Toxicity 0.000 claims 2
- 230000002246 oncogenic effect Effects 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 201000000849 skin cancer Diseases 0.000 claims 2
- 201000010153 skin papilloma Diseases 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 241000701161 unidentified adenovirus Species 0.000 claims 2
- 241001430294 unidentified retrovirus Species 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- PJURXISNSSBKOX-UHFFFAOYSA-N 6-bromo-n-(1h-indol-5-yl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=C2NC=CC2=CC(NC2C=3NC4=CC=C(C=C4C=3CCC2)Br)=C1 PJURXISNSSBKOX-UHFFFAOYSA-N 0.000 claims 1
- 206010004146 Basal cell carcinoma Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 206010061523 Lip and/or oral cavity cancer Diseases 0.000 claims 1
- 208000032271 Malignant tumor of penis Diseases 0.000 claims 1
- 208000003445 Mouth Neoplasms Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 208000002471 Penile Neoplasms Diseases 0.000 claims 1
- 206010034299 Penile cancer Diseases 0.000 claims 1
- 206010038111 Recurrent cancer Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 206010047741 Vulval cancer Diseases 0.000 claims 1
- 208000004354 Vulvar Neoplasms Diseases 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 208000003373 basosquamous carcinoma Diseases 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- MUGWFLQSVCKKOW-UHFFFAOYSA-N n-pyrimidin-2-yl-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=2NC3=CC=CC=C3C=2CCCC1NC1=NC=CC=N1 MUGWFLQSVCKKOW-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 208000001307 recurrent respiratory papillomatosis Diseases 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 206010046885 vaginal cancer Diseases 0.000 claims 1
- 208000013139 vaginal neoplasm Diseases 0.000 claims 1
- 201000005102 vulva cancer Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47725103P | 2003-06-10 | 2003-06-10 | |
| US49782303P | 2003-08-26 | 2003-08-26 | |
| PCT/US2004/017660 WO2004110999A1 (en) | 2003-06-10 | 2004-06-07 | Tetrahydrocarbazole derivatives and their pharmaceutical use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007501284A JP2007501284A (ja) | 2007-01-25 |
| JP2007501284A5 true JP2007501284A5 (https=) | 2007-08-02 |
Family
ID=33555453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006533561A Pending JP2007501284A (ja) | 2003-06-10 | 2004-06-07 | テトラヒドロカルバゾール誘導体およびそれらの薬学的使用 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7351733B2 (https=) |
| EP (1) | EP1654228B1 (https=) |
| JP (1) | JP2007501284A (https=) |
| KR (1) | KR20060017545A (https=) |
| AT (1) | ATE411981T1 (https=) |
| AU (1) | AU2004247676A1 (https=) |
| BR (1) | BRPI0411085A (https=) |
| CA (1) | CA2528321A1 (https=) |
| CO (1) | CO5660287A2 (https=) |
| DE (1) | DE602004017326D1 (https=) |
| ES (1) | ES2314446T3 (https=) |
| IL (1) | IL171974A0 (https=) |
| MA (1) | MA27880A1 (https=) |
| NO (1) | NO20055741L (https=) |
| RU (1) | RU2318810C2 (https=) |
| WO (1) | WO2004110999A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7622494B2 (en) | 2003-08-26 | 2009-11-24 | Smithkline Beecham Corporation | Chemical compounds |
| MXPA06010543A (es) | 2004-03-15 | 2007-03-26 | Ptc Therapeutics Inc | Derivados de carbolina utiles en la inhibicion de la angiogenesis. |
| US7767689B2 (en) | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
| US8076352B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| US8076353B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
| WO2006012310A2 (en) * | 2004-06-25 | 2006-02-02 | Genzyme Corporation | Carbazole derivatives for treating polycystic kidney disease |
| JP2008520675A (ja) * | 2004-11-22 | 2008-06-19 | スミスクライン ビーチャム コーポレーション | Ｈｃｖ阻害剤 |
| US8143257B2 (en) * | 2004-11-23 | 2012-03-27 | Ptc Therapeutics, Inc. | Substituted phenols as active agents inhibiting VEGF production |
| WO2007002051A1 (en) * | 2005-06-22 | 2007-01-04 | Smithkline Beecham Corporation | Carboline derivatives and their use as inhibitors of flaviviridae infections |
| WO2013139929A1 (en) * | 2012-03-22 | 2013-09-26 | Ludwig-Maximilians-Universität München | Novel means and methods for treating diseases of the central nervous system, metabolic and cardiac diseases and aging |
| WO2013177241A1 (en) | 2012-05-22 | 2013-11-28 | Trustees Of Dartmouth College | Method for synthesizing cycloalkanyl(b}indoles, cycloalkanyl(b) benzofurans, cycloalkanyl(b)benzothiophenes, compounds and methods of use |
| EP2690091A1 (en) | 2012-07-25 | 2014-01-29 | Studiengesellschaft Kohle mbH | Process for preparing substituted indole derivatives |
| KR101671484B1 (ko) | 2016-07-21 | 2016-11-01 | 김정환 | 오셀타미비르(Oseltamivir)를 포함하는 인유두종 바이러스 치료용 약학적 조성물 |
| US10882821B1 (en) | 2017-09-26 | 2021-01-05 | The Board Of Trustees Of The Leland Stanford Junior University | Enantiomeric compound for the reduction of the deleterious activity of extended nucleotide repeat containing genes |
| WO2021183980A1 (en) * | 2020-03-13 | 2021-09-16 | Fmc Corporation | Substituted pyrimidines and triazines as herbicides |
| CN113995758B (zh) * | 2021-11-04 | 2023-06-02 | 中山大学 | 咔唑-嘧啶衍生物在制备治疗抗肿瘤药物中的应用 |
| KR102907984B1 (ko) | 2022-11-22 | 2026-01-06 | 이경엽 | 알칼로이드 함유 인유두종 바이러스 감염의 예방 또는 치료용 조성물 |
| KR102907985B1 (ko) | 2022-11-22 | 2026-01-06 | 이경엽 | 인유두종 바이러스 감염에 의한 후두유두종의 예방 또는 치료용 조성물 |
| EP4725481A1 (en) * | 2024-10-10 | 2026-04-15 | Leibniz-Institut für Virologie | 1,2,3,4-tetrahydrocarbazole derivatives for use in treating an adenoviral infection |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE507797C (de) * | 1927-05-14 | 1930-09-20 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von 1-Aminocarbazol und seinen Derivaten |
| GB8924392D0 (en) * | 1989-10-30 | 1989-12-20 | Bayer Ag | Substituted cycloalkano/b/dihydroindole-and-indolesulphonamides |
| GB9008108D0 (en) * | 1990-04-10 | 1990-06-06 | Bayer Ag | Cycloalkano(b)dihydroindoles and-indolesulphonamides substituted by heterocycles |
| US5100891A (en) | 1991-01-18 | 1992-03-31 | Hoechst-Roussel Pharmaceuticals Inc. | Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[B]indoles and related compounds |
| CA2106642C (en) * | 1992-10-14 | 2005-08-16 | Peter Bod | Carbazolone derivatives and process for preparing the same |
| US6045398A (en) * | 1995-07-10 | 2000-04-04 | International Business Machines Corporation | Battery accepting unit and battery pack |
| GB0015904D0 (en) * | 2000-06-28 | 2000-08-23 | Hoffmann La Roche | Inhibitors of HPV E1 helicase enzyme |
| NZ533430A (en) * | 2001-12-14 | 2005-12-23 | Zentaris Gmbh | Tetrahydrocarbozole derivatives as ligands for G-protein coupled receptors (GPCR) |
| DE10164564B4 (de) * | 2001-12-14 | 2007-05-16 | Zentaris Gmbh | Tetrahydrocarbazolderivate als Liganden für G-Protein gekoppelte Rezeptoren (GPCR) |
-
2004
- 2004-06-07 KR KR1020057023781A patent/KR20060017545A/ko not_active Withdrawn
- 2004-06-07 JP JP2006533561A patent/JP2007501284A/ja active Pending
- 2004-06-07 WO PCT/US2004/017660 patent/WO2004110999A1/en not_active Ceased
- 2004-06-07 DE DE602004017326T patent/DE602004017326D1/de not_active Expired - Lifetime
- 2004-06-07 AT AT04776279T patent/ATE411981T1/de not_active IP Right Cessation
- 2004-06-07 RU RU2005138124/04A patent/RU2318810C2/ru not_active IP Right Cessation
- 2004-06-07 CA CA002528321A patent/CA2528321A1/en not_active Abandoned
- 2004-06-07 AU AU2004247676A patent/AU2004247676A1/en not_active Abandoned
- 2004-06-07 BR BRPI0411085-4A patent/BRPI0411085A/pt not_active IP Right Cessation
- 2004-06-07 US US10/560,013 patent/US7351733B2/en not_active Expired - Fee Related
- 2004-06-07 ES ES04776279T patent/ES2314446T3/es not_active Expired - Lifetime
- 2004-06-07 EP EP04776279A patent/EP1654228B1/en not_active Expired - Lifetime
-
2005
- 2005-11-15 IL IL171974A patent/IL171974A0/en unknown
- 2005-12-05 NO NO20055741A patent/NO20055741L/no not_active Application Discontinuation
- 2005-12-09 MA MA28646A patent/MA27880A1/fr unknown
- 2005-12-15 CO CO05126713A patent/CO5660287A2/es not_active Application Discontinuation
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