CA1299577C - Acides tetrahydrocarbazole-1-alcanoiques - Google Patents

Acides tetrahydrocarbazole-1-alcanoiques

Info

Publication number: CA1299577C
Authority: CA; Canada
Prior art keywords: chlorobenzyl; acetic acid; alkyl; phenyl; tetrahydro
Prior art date: 1987-01-09
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 - Lifetime

Application number

CA000527083A

Other languages

English (en)

Inventor

John W. Gillard

Yvan Guindon

Christiane Yoakim

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 Frosst Canada and Co

Original Assignee

Merck Frosst Canada and Co

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.)

1987-01-09

Filing date

1987-01-09

Publication date

1992-04-28

1987-01-09 Application filed by Merck Frosst Canada and Co filed Critical Merck Frosst Canada and Co

1987-01-09 Priority to CA000527083A priority Critical patent/CA1299577C/fr

1992-04-28 Application granted granted Critical

1992-04-28 Publication of CA1299577C publication Critical patent/CA1299577C/fr

2009-04-28 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000002253 acid Substances 0.000 title abstract description 14
XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 title abstract description 5
150000007513 acids Chemical class 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 163
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 91
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 44
125000000217 alkyl group Chemical group 0.000 claims abstract description 36
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 13
150000002367 halogens Chemical class 0.000 claims abstract description 13
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
125000001424 substituent group Chemical group 0.000 claims abstract description 11
150000003180 prostaglandins Chemical class 0.000 claims abstract description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims abstract description 7
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 7
125000002252 acyl group Chemical group 0.000 claims abstract description 6
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract description 3
125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 3
125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
239000000203 mixture Substances 0.000 claims description 41
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 38
239000004480 active ingredient Substances 0.000 claims description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
239000008194 pharmaceutical composition Substances 0.000 claims description 19
239000003112 inhibitor Substances 0.000 claims description 15
230000015572 biosynthetic process Effects 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 13
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 11
150000002617 leukotrienes Chemical class 0.000 claims description 9
239000002089 prostaglandin antagonist Substances 0.000 claims description 9
LHJWQVJJSYPRIX-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6-fluoro-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound OC(=O)CC1CCCC(C2=CC(F)=CC=C22)=C1N2CC1=CC=C(Cl)C=C1 LHJWQVJJSYPRIX-UHFFFAOYSA-N 0.000 claims description 7
229940094443 oxytocics prostaglandins Drugs 0.000 claims description 7
BRIAEVLTRZHLAS-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6,8-difluoro-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound OC(=O)CC1CCCC(C2=CC(F)=CC(F)=C22)=C1N2CC1=CC=C(Cl)C=C1 BRIAEVLTRZHLAS-UHFFFAOYSA-N 0.000 claims description 6
238000003786 synthesis reaction Methods 0.000 claims description 6
LJQDNXIQKNABMG-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-8-methyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(C)=CC=CC=2C=2CCCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 LJQDNXIQKNABMG-UHFFFAOYSA-N 0.000 claims description 5
239000005541 ACE inhibitor Substances 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
229960000905 indomethacin Drugs 0.000 claims description 5
IXHODLPXDHLVRY-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-8-fluoro-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound OC(=O)CC1CCCC(C2=CC=CC(F)=C22)=C1N2CC1=CC=C(Cl)C=C1 IXHODLPXDHLVRY-UHFFFAOYSA-N 0.000 claims description 4
239000000730 antalgic agent Substances 0.000 claims description 4
239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 4
AZZZVAUBRCDMFI-UHFFFAOYSA-N 2-(2,3,4,9-tetrahydro-1h-carbazol-1-yl)acetic acid Chemical compound N1C2=CC=CC=C2C2=C1C(CC(=O)O)CCC2 AZZZVAUBRCDMFI-UHFFFAOYSA-N 0.000 claims description 3
108010069102 Thromboxane-A synthase Proteins 0.000 claims description 3
229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 claims description 3
230000002401 inhibitory effect Effects 0.000 claims description 3
239000002599 prostaglandin synthase inhibitor Substances 0.000 claims description 3
YKHYHARVNMABLJ-UHFFFAOYSA-N 2-(9-benzyl-6-fluoro-1,2,3,4-tetrahydrocarbazol-1-yl)acetic acid Chemical compound OC(=O)CC1CCCC(C2=CC(F)=CC=C22)=C1N2CC1=CC=CC=C1 YKHYHARVNMABLJ-UHFFFAOYSA-N 0.000 claims description 2
HGJXDGZPRZBNMM-UHFFFAOYSA-N 2-[6,8-dichloro-9-[(4-chlorophenyl)methyl]-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound OC(=O)CC1CCCC(C2=CC(Cl)=CC(Cl)=C22)=C1N2CC1=CC=C(Cl)C=C1 HGJXDGZPRZBNMM-UHFFFAOYSA-N 0.000 claims description 2
UTQJWOLGMMNTFJ-UHFFFAOYSA-N 2-[6-bromo-9-[(4-chlorophenyl)methyl]-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound OC(=O)CC1CCCC(C2=CC(Br)=CC=C22)=C1N2CC1=CC=C(Cl)C=C1 UTQJWOLGMMNTFJ-UHFFFAOYSA-N 0.000 claims description 2
AEIQZZAOZDLCSH-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound OC(=O)CC1CCCC(C2=CC=CC=C22)=C1N2CC1=CC=C(Cl)C=C1 AEIQZZAOZDLCSH-UHFFFAOYSA-N 0.000 claims description 2
QCAMKFJRGYDIEF-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6,8-difluoro-1,2,3,4-tetrahydrocarbazol-1-yl]ethanol Chemical compound OCCC1CCCC(C2=CC(F)=CC(F)=C22)=C1N2CC1=CC=C(Cl)C=C1 QCAMKFJRGYDIEF-UHFFFAOYSA-N 0.000 claims description 2
NFTRFQUCIXZJLP-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6-(trifluoromethyl)-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound OC(=O)CC1CCCC(C2=CC(=CC=C22)C(F)(F)F)=C1N2CC1=CC=C(Cl)C=C1 NFTRFQUCIXZJLP-UHFFFAOYSA-N 0.000 claims description 2
FQBJTRFMENJMIM-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6-fluoro-1,2,3,4-tetrahydrocarbazol-1-yl]ethanol Chemical compound OCCC1CCCC(C2=CC(F)=CC=C22)=C1N2CC1=CC=C(Cl)C=C1 FQBJTRFMENJMIM-UHFFFAOYSA-N 0.000 claims description 2
TYKGPOJVFWJYEV-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6-methyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(CC(O)=O)CCCC=2C2=CC(C)=CC=C2N1CC1=CC=C(Cl)C=C1 TYKGPOJVFWJYEV-UHFFFAOYSA-N 0.000 claims description 2
WWOUNKQAHBHPNZ-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6-methylsulfanyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(CC(O)=O)CCCC=2C2=CC(SC)=CC=C2N1CC1=CC=C(Cl)C=C1 WWOUNKQAHBHPNZ-UHFFFAOYSA-N 0.000 claims description 2
LJSNYHVKSOASHD-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6-methylsulfinyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(CC(O)=O)CCCC=2C2=CC(S(=O)C)=CC=C2N1CC1=CC=C(Cl)C=C1 LJSNYHVKSOASHD-UHFFFAOYSA-N 0.000 claims description 2
HFESGUZYQCETPW-UHFFFAOYSA-N 3-[9-[(4-chlorophenyl)methyl]-6-fluoro-1,2,3,4-tetrahydrocarbazol-1-yl]propanoic acid Chemical compound OC(=O)CCC1CCCC(C2=CC(F)=CC=C22)=C1N2CC1=CC=C(Cl)C=C1 HFESGUZYQCETPW-UHFFFAOYSA-N 0.000 claims description 2
COHMMVIFRSXCHX-UHFFFAOYSA-N 3-[9-[(4-chlorophenyl)methyl]-6-methoxy-1,2,3,4-tetrahydrocarbazol-1-yl]propan-1-ol Chemical compound C1=2C(CCCO)CCCC=2C2=CC(OC)=CC=C2N1CC1=CC=C(Cl)C=C1 COHMMVIFRSXCHX-UHFFFAOYSA-N 0.000 claims description 2
JLAIZOLFEYBVSF-UHFFFAOYSA-N 3-[9-[(4-chlorophenyl)methyl]-6-methoxy-1,2,3,4-tetrahydrocarbazol-1-yl]propanoic acid Chemical compound C1=2C(CCC(O)=O)CCCC=2C2=CC(OC)=CC=C2N1CC1=CC=C(Cl)C=C1 JLAIZOLFEYBVSF-UHFFFAOYSA-N 0.000 claims description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 6
102000003834 Histamine H1 Receptors Human genes 0.000 claims 2
108090000110 Histamine H1 Receptors Proteins 0.000 claims 2
230000002093 peripheral effect Effects 0.000 claims 2
229940044551 receptor antagonist Drugs 0.000 claims 2
239000002464 receptor antagonist Substances 0.000 claims 2
YQCDAHAEWCGZEL-UHFFFAOYSA-N 2-[5,7-dichloro-9-[(4-chlorophenyl)methyl]-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound OC(=O)CC1CCCC(C2=C(Cl)C=C(Cl)C=C22)=C1N2CC1=CC=C(Cl)C=C1 YQCDAHAEWCGZEL-UHFFFAOYSA-N 0.000 claims 1
ZXFYVCPNRDYBQS-UHFFFAOYSA-N 2-[6-chloro-9-[(4-chlorophenyl)methyl]-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound OC(=O)CC1CCCC(C2=CC(Cl)=CC=C22)=C1N2CC1=CC=C(Cl)C=C1 ZXFYVCPNRDYBQS-UHFFFAOYSA-N 0.000 claims 1
CFKFSLVFCHVITQ-UHFFFAOYSA-N 2-[6-fluoro-9-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1CN1C2=CC=C(F)C=C2C2=C1C(CC(O)=O)CCC2 CFKFSLVFCHVITQ-UHFFFAOYSA-N 0.000 claims 1
ZKUIAARNPJRBCL-UHFFFAOYSA-N 2-[6-tert-butyl-9-[(4-chlorophenyl)methyl]-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(CC(O)=O)CCCC=2C2=CC(C(C)(C)C)=CC=C2N1CC1=CC=C(Cl)C=C1 ZKUIAARNPJRBCL-UHFFFAOYSA-N 0.000 claims 1
HXZXEQRLFOFUSY-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-5-fluoro-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound OC(=O)CC1CCCC(C2=C(F)C=CC=C22)=C1N2CC1=CC=C(Cl)C=C1 HXZXEQRLFOFUSY-UHFFFAOYSA-N 0.000 claims 1
MIGIIILWBPGFJA-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6,8-dimethyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(CC(O)=O)CCCC=2C2=CC(C)=CC(C)=C2N1CC1=CC=C(Cl)C=C1 MIGIIILWBPGFJA-UHFFFAOYSA-N 0.000 claims 1
NPUJXGKDOJOCHF-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6-fluoro-3-methyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1C(C)CC(CC(O)=O)C2=C1C1=CC(F)=CC=C1N2CC1=CC=C(Cl)C=C1 NPUJXGKDOJOCHF-UHFFFAOYSA-N 0.000 claims 1
IVQSKBHKYSVIOS-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(CC(O)=O)CCCC=2C2=CC(OC)=CC(C)=C2N1CC1=CC=C(Cl)C=C1 IVQSKBHKYSVIOS-UHFFFAOYSA-N 0.000 claims 1
OKONXEMKRUEWBR-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(CC(O)=O)CCCC=2C2=CC(S(=O)(=O)C)=CC=C2N1CC1=CC=C(Cl)C=C1 OKONXEMKRUEWBR-UHFFFAOYSA-N 0.000 claims 1
AIHZFGCMKOUUOO-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-6-propan-2-yl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(CC(O)=O)CCCC=2C2=CC(C(C)C)=CC=C2N1CC1=CC=C(Cl)C=C1 AIHZFGCMKOUUOO-UHFFFAOYSA-N 0.000 claims 1
CGSLOOCFBLEGKW-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-8-methylsulfanyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(SC)=CC=CC=2C=2CCCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 CGSLOOCFBLEGKW-UHFFFAOYSA-N 0.000 claims 1
BRVYETPRGCQZJA-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-8-methylsulfinyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(S(=O)C)=CC=CC=2C=2CCCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 BRVYETPRGCQZJA-UHFFFAOYSA-N 0.000 claims 1
YNLWPJVDHZFCOY-UHFFFAOYSA-N 2-[9-[(4-chlorophenyl)methyl]-8-propan-2-yl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1=2C(C(C)C)=CC=CC=2C=2CCCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 YNLWPJVDHZFCOY-UHFFFAOYSA-N 0.000 claims 1
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XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
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150000002431 hydrogen Chemical group 0.000 description 1
PVKDFUXBDJPRGU-UHFFFAOYSA-N hydron;4-(2-imidazol-1-ylethoxy)benzoic acid;chloride Chemical compound Cl.C1=CC(C(=O)O)=CC=C1OCCN1C=NC=C1 PVKDFUXBDJPRGU-UHFFFAOYSA-N 0.000 description 1
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QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
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238000007726 management method Methods 0.000 description 1
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HNJJXZKZRAWDPF-UHFFFAOYSA-N methapyrilene Chemical group C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CS1 HNJJXZKZRAWDPF-UHFFFAOYSA-N 0.000 description 1
QDJUNKKRMRBNKD-UHFFFAOYSA-N methyl 2-(5-tert-butyl-2-oxocyclohexyl)acetate Chemical compound COC(=O)CC1CC(C(C)(C)C)CCC1=O QDJUNKKRMRBNKD-UHFFFAOYSA-N 0.000 description 1
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239000001923 methylcellulose Substances 0.000 description 1
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239000007932 molded tablet Substances 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
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210000004877 mucosa Anatomy 0.000 description 1
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208000010125 myocardial infarction Diseases 0.000 description 1
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ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
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239000007764 o/w emulsion Substances 0.000 description 1
SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 1
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210000000056 organ Anatomy 0.000 description 1
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GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
229960000620 ranitidine Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
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150000003335 secondary amines Chemical class 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229940080237 sodium caseinate Drugs 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
XBTIPIZROJAKOJ-UHFFFAOYSA-M sodium;5-(pyridin-3-ylmethyl)-1-benzofuran-2-carboxylate Chemical compound [Na+].C=1C=C2OC(C(=O)[O-])=CC2=CC=1CC1=CC=CN=C1 XBTIPIZROJAKOJ-UHFFFAOYSA-M 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000002602 strong irritant Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
229960000351 terfenadine Drugs 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
229960004559 theobromine Drugs 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
CUWHXIJMTMMRTI-UHFFFAOYSA-N thiadiazol-4-amine Chemical class NC1=CSN=N1 CUWHXIJMTMMRTI-UHFFFAOYSA-N 0.000 description 1
DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
JKVRTUCVPZTEQZ-UHFFFAOYSA-N tributyltin azide Chemical compound CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-] JKVRTUCVPZTEQZ-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
229940038773 trisodium citrate Drugs 0.000 description 1
230000001562 ulcerogenic effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
229960003414 zomepirac Drugs 0.000 description 1

Classifications

- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000527083A 1987-01-09 1987-01-09 Acides tetrahydrocarbazole-1-alcanoiques Expired - Lifetime CA1299577C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000527083A CA1299577C (fr)	1987-01-09	1987-01-09	Acides tetrahydrocarbazole-1-alcanoiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000527083A CA1299577C (fr)	1987-01-09	1987-01-09	Acides tetrahydrocarbazole-1-alcanoiques

Publications (1)

Publication Number	Publication Date
CA1299577C true CA1299577C (fr)	1992-04-28

Family

ID=4134725

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000527083A Expired - Lifetime CA1299577C (fr)	1987-01-09	1987-01-09	Acides tetrahydrocarbazole-1-alcanoiques

Country Status (1)

Country	Link
CA (1)	CA1299577C (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005033112A3 (fr) *	2003-10-02	2005-06-09	Salmedix Inc	Derives d'indole substitues
US7105560B1 (en)	1999-07-23	2006-09-12	The Regents Of The University Of California	Use of etodolac in the treatment of multiple myeloma
US7151100B1 (en)	1999-07-23	2006-12-19	The Regents Of The University Of California	Indole compounds useful for the treatment of cancer
US7189752B2 (en)	1999-07-23	2007-03-13	Carson Dennis A	Use of etodolac for the treatment of chronic lymphocytic leukemia
US7211599B2 (en)	2002-09-19	2007-05-01	The Regents Of The University Of California	Use of etodolac to treat hyperplasia
EP1697322A4 (fr) *	2003-12-15	2007-12-26	Merck Frosst Canada Ltd	Derives de tetrahydrocarbazole et de cyclopentanoindole substitues
US7361680B2 (en)	1999-07-23	2008-04-22	The Regents Of The University Of California	Indole compounds useful for the treatment of cancer

1987
- 1987-01-09 CA CA000527083A patent/CA1299577C/fr not_active Expired - Lifetime

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7105560B1 (en)	1999-07-23	2006-09-12	The Regents Of The University Of California	Use of etodolac in the treatment of multiple myeloma
US7151100B1 (en)	1999-07-23	2006-12-19	The Regents Of The University Of California	Indole compounds useful for the treatment of cancer
US7189752B2 (en)	1999-07-23	2007-03-13	Carson Dennis A	Use of etodolac for the treatment of chronic lymphocytic leukemia
US7361680B2 (en)	1999-07-23	2008-04-22	The Regents Of The University Of California	Indole compounds useful for the treatment of cancer
US7211599B2 (en)	2002-09-19	2007-05-01	The Regents Of The University Of California	Use of etodolac to treat hyperplasia
WO2005033112A3 (fr) *	2003-10-02	2005-06-09	Salmedix Inc	Derives d'indole substitues
WO2005033113A3 (fr) *	2003-10-02	2005-06-30	Salmedix Inc	Derives indoles
US7314886B2 (en)	2003-10-02	2008-01-01	Cephalon, Inc.	Tetrahydropyrano-indole derivatives
US7446122B2 (en)	2003-10-02	2008-11-04	Cephalon, Inc.	Substituted indole derivatives
EP1697322A4 (fr) *	2003-12-15	2007-12-26	Merck Frosst Canada Ltd	Derives de tetrahydrocarbazole et de cyclopentanoindole substitues

Legal Events

Date	Code	Title	Description
1994-10-28	MKLA	Lapsed

Publication	Publication Date	Title
US4808608A (en)	1989-02-28	Tetrahydrocarbazole 1-alkanoic acids, pharmaceutical compositions and use
AU592615B2 (en)	1990-01-18	Tetrahydrocarbazol-1-alkanoic acids
EP0275667B1 (fr)	1992-03-18	N-Benzyl-indoles hétérosubstitués en position 3
US5081145A (en)	1992-01-14	Indole-2-alkanoic acids compositions of and anti allergic use thereof
EP1339679A1 (fr)	2003-09-03	Derives de 3-aroylindole et leur utilisation en tant qu'agonistes des recepteurs cb2
LU86406A1 (fr)	1986-11-05	Imidazoquinoleines antithrombogenes cardiotoniques
JPS6163653A (ja)	1986-04-01	インド−ル−２−アルカン酸類
CZ285476B6 (cs)	1999-08-11	Heterocyklické aromatické oxazolové sloučeniny, jejich oximové, ketonové, ketomethylenové, esterové a amidové sloučeniny a farmaceutické přípravky, inhibitory cyklooxygenasy a protizánětlivá činidla obsahující tyto oxazolové sloučeniny
US4940719A (en)	1990-07-10	Tetrahydrocarbazole esters, pharmaceutical compositions and use
JP2006510673A (ja)	2006-03-30	プラスミノゲンアクティベータインヒビター１（ｐａｉ−１）のインヒビターとしての、アリール、アリールオキシ、および、アルキルオキシ置換１ｈ−インドール−３−イルグリオキシル酸誘導体
JP2003501464A (ja)	2003-01-14	シクロオキシゲナーゼ−２の阻害剤としての１−（４−スルファミルアリール）−３−置換−５−アリール−２−ピラゾリン
CA1299577C (fr)	1992-04-28	Acides tetrahydrocarbazole-1-alcanoiques
JPH0641095A (ja)	1994-02-15	置換トリアゾロンおよびトリアゾールジオンの抗うつ性３−ハロフェニルピペラジニル−プロピル誘導体
US4775680A (en)	1988-10-04	Cyclohept[b]indolealkanoic acids, pharmaceutical compositions and use
CA1326030C (fr)	1994-01-11	Acides cyclohept[b]indole alcanoiques
EP0239306B1 (fr)	1993-06-02	Esters de tétrahydrocarbazoles
JP3465827B2 (ja)	2003-11-10	アザインドール誘導体およびこれを有効成分とする抗潰瘍薬
US7250434B2 (en)	2007-07-31	CCK-1 receptor modulators
HU187634B (en)	1986-02-28	Process for producing alkanolamine derivatives
CA1305485C (fr)	1992-07-21	Acides tetrahydrocarbazole-1-alcanoiques
US4906654A (en)	1990-03-06	Cyclohept[b]indoleakanoic acids, pharmaceutical compositions and use
CA1330090C (fr)	1994-06-07	Esters de type tetrahydrocarbazole
BE1009376A4 (fr)	1997-03-04	Derives du carboxymethylidenecycloheptimidazole, procede de preparation de ces derniers et agents therapeutiques contenant ces composes.
CA1334415C (fr)	1995-02-14	3-hetero-a substituant-n-benzyl-indoles
FR2639944A1 (fr)	1990-06-08	Nouveaux derives de l'indole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent