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US 7,030,109 B2Granted
1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position
AssigneePharmacia & Upjohn Company
InventorsEric Jon Jacobsen, Kalpana M. Merchant
Life of this patent
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Abstract
The present invention discloses radioligands of 9-arylsulfone of the formula (X) or a pharmaceutically acceptable salt or enantiomer thereof, which are useful in diagnosing depression, obesity and other CNS disorders.
Claims17
An isotopically labeled compound of formula (X)
- or a pharmaceutically acceptable salt or enantiomer thereof
- wherein R3 is:
- (1) —H,
- (2) C1–C4 alkyl,
- (3) C0–C4 alkyl-φ where -φ is optionally substituted with up to 2 of the following:
- (a) —F, —Cl, —Br, —I,
- (b) —OH,
- (c) —OC1–C4 alkyl,
- (d) —CF3,
- (e) —C≡N,
- (f) —NO2,
- where RN is:
- (1) —H,
- (2) C1–C4 alkyl,
- (3) C0–C4 alkyl-φ where -φ is optionally substituted with up to 2 of the following:
- (a) —F, —Cl, —Br, —I,
- (b) —O—RN-1 where RN-1 is —H, C1–C4 alkyl, and -φ,
- (c) —CF3,
- (d) —C≡N,
- (e) —NO2,
- where R9 is:
- (1) —H,
- (2) —F, —Cl,
- (3) C1–C4 alkyl,
- (4) C1–C3 alkoxy,
- (5) —CF3,
- (6) C0–C4 alkyl–φwhere -φ is optionally substituted with up to 2 of the following:
- (a) —F, —Cl, —Br, —I,
- (b) —O—R9-1 where R9-1 is —H, C1–C4 alkyl, and -φ,
- (c) —CF3,
- (d) —C≡N,
- (e) —NO2
- (7) —OR9-1 where R9-1 is as defined above,
- wherein the compound of formula X has an isotopic label.
31 more elements
A compound, wherein the compound is:
- 3,6-dimcthyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepin [4,5-b]indole, and
- 3-methyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole, wherein the compound has an isotopic label.
A compound, wherein the compound is:
- 1-methyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[45-b]indole,
- 2-methyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole.
- 4-methyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole,
- 5-nethyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole,
- 1,6-dimethyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole,
- 2,6-dimethyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole,
- 4,6-dimethyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole, and
- 5,6-dimethyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole, wherein the compound has an isotopic (abel.
5 more elements
A protected 9-arylsulfone of formula (VIII)
- or a pharmaceutically acceptable salt or enantiomer thereof wherein PG is:
- (1) φ—CH2—,
- (2) φ—CO—,
- (3) φ—CH2—CO2—, and
- (4) —CO—O—C(CH3)3;
- where R9 is:
- (1) —H,
- (2) —F, —Cl,
- (3) C1–C4 alkyl,
- (4) C1–C3 alkoxy,
- (5) —CF3,
- (6) C0–C4 alkyl-φ where -φ is optionally substituted with up to 2 of the following:
- (a) —F, —Cl, —Br, —I,
- (b) —O—R9-1 where R9-1 is —H, C1–C4 alkyl, and -φ,
- (c) —CF3,
- (d) —C≡N,
- (e) —NO2
- (7) —OR9-1 where R9-1 is as deined above,
- wherein the compound of formula VIII has an isotopic label.
16 more elements
Dependencies are inferred from the claim text.