Patent US4235423A successfully refreshed from Google Patents.
US4059583A
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Substituted indoles
Assignee: Janssen Pharmaceuticals Inc
•
Filing: 1976-10-13
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Granted: 1977-11-22
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Expires: 1996-10-13
Abstract
Abstract Substituted thioindoles and their sulfoxide and sulfone derivatives, useful as cardiac rate lowering agents and for other pharmacological properties, and precursors therefor.
Inventors
- 👤 David Fred McComsey
- 👤 Michael John Zelesko
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 15:04
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24
Claims Analysis
Total Claims: 70
Claim 1
Independent Claim
430 words
A member selected from the group consisting of a compound having a formula selected from the group consisting of: ##STR57## and ##STR58## and the therapeutically active acid addition salts thereof, wherein: X and X 1 are each members selected from the group consisting of hydrogen, loweralkyl, loweralkoxy, halo, loweralkylamino and acylamino; provided that X and X 1 are not both acylamino; R 1 is a member selected from the group consisting of hydrogen, loweralkyl, cycloalkyl, phenyl, substituted phenyl, phenylloweralkyl, substituted phenylloweralkyl wherein said substitution is on only the phenyl portion, loweralkoxyloweralkyl, alkenyl, alkynyl, cycloalkylloweralkyl, and cycloalkenyl; R 2 is a member selected from the group consisting of hydrogen, loweralkyl, phenyl, biphenyl, naphthyl, substituted phenyl, heterocyclic aryl, phenylloweralkyl, and substituted phenylloweralkyl wherein said substitution is on only the phenyl portion; Z is a member selected from the group consisting of thio, sulfinyl, and sulfonyl; n is the integer 1, 2, or 3; R 3 is a member selected from the group consisting of hydrogen and loweralkyl; R 4 is a member selected from the group consisting of hydrogen, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, substituted phenylloweralkyl wherein said substitution is on only the phenyl portion, cycloalkyl, hydroxyloweralkyl, and alkenyl; A and B taken individually are each loweralkyl; A and B taken together is a member selected from the group consisting of --CH 2 CH(R 5 )CH 2 --, --CH 2 CH 2 CH(R 5 )--, --N(R 6 )CH(R 5 )(CH 2 ) m --, --(CH 2 ) 4 --, and --(CH 2 ) 5 --, said R 5 being a member selected from the group consisting of hydrogen, loweralkyl, phenyl, and substituted phenyl, said R 6 being a member selected from the group consisting of hydrogen and lower-alkyl, and said m being 1 or 2; provided that when m is 2, R 5 is H; said cycloalkyl having from 3 to about 8 carbon atoms, said alkenyl having from 2 to about 5 carbon atoms; said alkynyl having from about 2 to about 5 carbon atoms; said cycloalkenyl having from 5 to about 7 carbon atoms; said cycloalkylloweralkyl having from 3 to about 8 carbon atoms in its cycloalkyl portion and from 1 to about 5 carbon atoms in its loweralkyl portion; said acyl consisting of loweralkyl carboxy radicals, phenyl carboxy radicals, and substituted phenyl carboxy radicals; said substituted phenyl being phenyl substituted with from 1 to 3 members each selected from the group consisting of loweralkyl, loweralkoxy, and halo; and said heterocyclic aryl comprising 5- to 10-membered heteroaromatics wherein the hetero atoms are one or more thia, aza or oxa atoms.
Claim 2
Dependent Claim
430 words
A member selected from the group consisting of a compound having a formula selected from the group consisting of: ##STR57## and ##STR58## and the therapeutically active acid addition salts thereof, wherein: X and X 1 are each members selected from the group consisting of hydrogen, loweralkyl, loweralkoxy, halo, loweralkylamino and acylamino; provided that X and X 1 are not both acylamino; R 1 is a member selected from the group consisting of hydrogen, loweralkyl, cycloalkyl, phenyl, substituted phenyl, phenylloweralkyl, substituted phenylloweralkyl wherein said substitution is on only the phenyl portion, loweralkoxyloweralkyl, alkenyl, alkynyl, cycloalkylloweralkyl, and cycloalkenyl; R 2 is a member selected from the group consisting of hydrogen, loweralkyl, phenyl, biphenyl, naphthyl, substituted phenyl, heterocyclic aryl, phenylloweralkyl, and substituted phenylloweralkyl wherein said substitution is on only the phenyl portion; Z is a member selected from the group consisting of thio, sulfinyl, and sulfonyl; n is the integer 1, 2, or 3; R 3 is a member selected from the group consisting of hydrogen and loweralkyl; R 4 is a member selected from the group consisting of hydrogen, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, substituted phenylloweralkyl wherein said substitution is on only the phenyl portion, cycloalkyl, hydroxyloweralkyl, and alkenyl; A and B taken individually are each loweralkyl; A and B taken together is a member selected from the group consisting of --CH 2 CH(R 5 )CH 2 --, --CH 2 CH 2 CH(R 5 )--, --N(R 6 )CH(R 5 )(CH 2 ) m --, --(CH 2 ) 4 --, and --(CH 2 ) 5 --, said R 5 being a member selected from the group consisting of hydrogen, loweralkyl, phenyl, and substituted phenyl, said R 6 being a member selected from the group consisting of hydrogen and lower-alkyl, and said m being 1 or 2; provided that when m is 2, R 5 is H; said cycloalkyl having from 3 to about 8 carbon atoms, said alkenyl having from 2 to about 5 carbon atoms; said alkynyl having from about 2 to about 5 carbon atoms; said cycloalkenyl having from 5 to about 7 carbon atoms; said cycloalkylloweralkyl having from 3 to about 8 carbon atoms in its cycloalkyl portion and from 1 to about 5 carbon atoms in its loweralkyl portion; said acyl consisting of loweralkyl carboxy radicals, phenyl carboxy radicals, and substituted phenyl carboxy radicals; said substituted phenyl being phenyl substituted with from 1 to 3 members each selected from the group consisting of loweralkyl, loweralkoxy, and halo; and said heterocyclic aryl comprising 5- to 10-membered heteroaromatics wherein the hetero atoms are one or more thia, aza or oxa atoms.
Claim 3
Dependent Claim
421 words
A member selected from the group consisting of a compound of formula: ##STR59## and the therapeutically active acid addition salts thereof, wherein: X and X 1 are each members selected from the group consisting of hydrogen, loweralkyl, loweralkoxy, halo, loweralkylamino and acylamino; provided that X and X 1 are not both acylamino; R 1 is a member selected from the group consisting of hydrogen, loweralkyl, cycloalkyl, phenyl, substituted phenyl, phenylloweralkyl, substituted phenylloweralkyl wherein said substitution is on only the phenyl portion, loweralkoxy loweralkyl, alkenyl, alkynyl, cycloalkylloweralkyl, and cycloalkenyl; R 2 is a member selected from the group consisting of hydrogen, loweralkyl, phenyl, biphenyl, naphthyl, substituted phenyl, heterocyclic aryl, phenylloweralkyl, and substituted phenylloweralkyl wherein said substitution is on only the phenyl portion; Z is a member selected from the group consisting of thio, sulfinyl, and sulfonyl; n is the integer 1, 2, or 3; R 3 is a member selected from the group consisting of hydrogen and loweralkyl; R 4 is a member selected from the group consisting of hydrogen, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, substituted phenylloweralkyl wherein said substitution is on only the phenyl portion, cycloalkyl, hydroxyloweralkyl, alkenyl, and alkynyl; A and B taken individually are each loweralkyl; A and B taken together is a member selected from the group consisting of --CH 2 CH(R 5 )CH 2 --, --CH 2 CH 2 CH(R 5 ), --N(R 6 )CH(R 5 )(CH 2 ) m --, --(CH 2 ) 4 --, and --(CH 2 ) 5 --, said R 5 being a member selected from the group consisting of hydrogen, phenyl, and substituted phenyl, said R 6 being a member selected from the group consisting of hydrogen and loweralkyl, said m being 1 or 2; provided that when n is 2, R 5 is H; said cycloalkyl having from 3 to about 8 carbon atoms, said alkenyl having from 2 to about 5 carbon atoms, said alkynyl having from about 2 to about 5 carbon atoms; said cycloalkenyl having from 5 to about 7 carbon atoms; said cycloalkylloweralkyl having from 3 to about 8 carbon atoms in its cycloalkyl portion and from 1 to about 5 carbon atoms in its loweralkyl portion; said acyl consisting of loweralkyl carboxy radicals; phenyl carboxy radicals, and substituted phenyl carboxy radicals; said substituted phenyl being phenyl substituted with from 1 to 3 members each selected from the group consisting of loweralkyl, loweralkoxy, and halo; and said heterocyclic aryl comprising 5- to 10-membered heteroaromatics wherein the hetero atoms are 1 or more thia, aza or oxa atoms.
Claim 4
Dependent Claim
421 words
A member selected from the group consisting of a compound of formula: ##STR59## and the therapeutically active acid addition salts thereof, wherein: X and X 1 are each members selected from the group consisting of hydrogen, loweralkyl, loweralkoxy, halo, loweralkylamino and acylamino; provided that X and X 1 are not both acylamino; R 1 is a member selected from the group consisting of hydrogen, loweralkyl, cycloalkyl, phenyl, substituted phenyl, phenylloweralkyl, substituted phenylloweralkyl wherein said substitution is on only the phenyl portion, loweralkoxy loweralkyl, alkenyl, alkynyl, cycloalkylloweralkyl, and cycloalkenyl; R 2 is a member selected from the group consisting of hydrogen, loweralkyl, phenyl, biphenyl, naphthyl, substituted phenyl, heterocyclic aryl, phenylloweralkyl, and substituted phenylloweralkyl wherein said substitution is on only the phenyl portion; Z is a member selected from the group consisting of thio, sulfinyl, and sulfonyl; n is the integer 1, 2, or 3; R 3 is a member selected from the group consisting of hydrogen and loweralkyl; R 4 is a member selected from the group consisting of hydrogen, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, substituted phenylloweralkyl wherein said substitution is on only the phenyl portion, cycloalkyl, hydroxyloweralkyl, alkenyl, and alkynyl; A and B taken individually are each loweralkyl; A and B taken together is a member selected from the group consisting of --CH 2 CH(R 5 )CH 2 --, --CH 2 CH 2 CH(R 5 ), --N(R 6 )CH(R 5 )(CH 2 ) m --, --(CH 2 ) 4 --, and --(CH 2 ) 5 --, said R 5 being a member selected from the group consisting of hydrogen, phenyl, and substituted phenyl, said R 6 being a member selected from the group consisting of hydrogen and loweralkyl, said m being 1 or 2; provided that when n is 2, R 5 is H; said cycloalkyl having from 3 to about 8 carbon atoms, said alkenyl having from 2 to about 5 carbon atoms, said alkynyl having from about 2 to about 5 carbon atoms; said cycloalkenyl having from 5 to about 7 carbon atoms; said cycloalkylloweralkyl having from 3 to about 8 carbon atoms in its cycloalkyl portion and from 1 to about 5 carbon atoms in its loweralkyl portion; said acyl consisting of loweralkyl carboxy radicals; phenyl carboxy radicals, and substituted phenyl carboxy radicals; said substituted phenyl being phenyl substituted with from 1 to 3 members each selected from the group consisting of loweralkyl, loweralkoxy, and halo; and said heterocyclic aryl comprising 5- to 10-membered heteroaromatics wherein the hetero atoms are 1 or more thia, aza or oxa atoms.
Claim 5
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 6
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 7
Dependent Claim
17 words
A member selected from the group consisting of 3-[3-(1-methyl-2-pyrrolidinylideneamino)propylthio]indole and the therapeutically active acid addition salts thereof.
Claim 8
Dependent Claim
17 words
A member selected from the group consisting of 3-[3-(1-methyl-2-pyrrolidinylideneamino)propylthio]indole and the therapeutically active acid addition salts thereof.
Claim 9
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)propylthio]indole and the therapeutically active acid addition salts thereof.
Claim 10
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)propylthio]indole and the therapeutically active acid addition salts thereof.
Claim 11
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-1-methylindole and the therapeutically active acid addition salts thereof.
Claim 12
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-1-methylindole and the therapeutically active acid addition salts thereof.
Claim 13
Dependent Claim
17 words
A member selected from the group consisting of 5-methoxy-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 14
Dependent Claim
17 words
A member selected from the group consisting of 5-methoxy-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 15
Dependent Claim
17 words
A member selected from the group consisting of 1-ethyl-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 16
Dependent Claim
17 words
A member selected from the group consisting of 1-ethyl-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 17
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-2-methylindole and the therapeutically active acid addition salts thereof.
Claim 18
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-2-methylindole and the therapeutically active acid addition salts thereof.
Claim 19
Dependent Claim
17 words
A member selected from the group consisting of 1,2-dimethyl-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 20
Dependent Claim
17 words
A member selected from the group consisting of 1,2-dimethyl-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 21
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-2-phenylindole and the therapeutically active acid addition salts thereof.
Claim 22
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-2-phenylindole and the therapeutically active acid addition salts thereof.
Claim 23
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-imidazolinylamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 24
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-imidazolinylamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 25
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylsulfinyl]indole and the therapeutically active acid addition salts thereof.
Claim 26
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylsulfinyl]indole and the therapeutically active acid addition salts thereof.
Claim 27
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino]ethylthio]-1-benzylindole and the therapeutically active acid addition salts thereof.
Claim 28
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino]ethylthio]-1-benzylindole and the therapeutically active acid addition salts thereof.
Claim 29
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-1-(2-methoxyethyl)indole and the therapeutically active acid addition salts thereof.
Claim 30
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-1-(2-methoxyethyl)indole and the therapeutically active acid addition salts thereof.
Claim 31
Dependent Claim
17 words
A member selected from the group consisting of 1-cyclopentyl-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 32
Dependent Claim
17 words
A member selected from the group consisting of 1-cyclopentyl-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 33
Dependent Claim
17 words
A member selected from the group consisting of 1-(2-furanylmethyl)-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 34
Dependent Claim
17 words
A member selected from the group consisting of 1-(2-furanylmethyl)-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 35
Dependent Claim
17 words
A member selected from the group consisting of 1-(cyclopropylmethyl)-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 36
Dependent Claim
17 words
A member selected from the group consisting of 1-(cyclopropylmethyl)-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 37
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-1-(2-propenyl)indole and the therapeutically active acid addition salts thereof.
Claim 38
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-1-(2-propenyl)indole and the therapeutically active acid addition salts thereof.
Claim 39
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-1-(n-octyl)indole and the therapeutically active acid addition salts thereof.
Claim 40
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-1-(n-octyl)indole and the therapeutically active acid addition salts thereof.
Claim 41
Dependent Claim
17 words
A member selected from the group consisting of 3-{2-[1-(dimethylamino)ethylideneamino]ethylthio}indole and the therapeutically active acid addition salts thereof.
Claim 42
Dependent Claim
17 words
A member selected from the group consisting of 3-{2-[1-(dimethylamino)ethylideneamino]ethylthio}indole and the therapeutically active acid addition salts thereof.
Claim 43
Dependent Claim
17 words
A member selected from the group consisting of 5-ethyl-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 44
Dependent Claim
17 words
A member selected from the group consisting of 5-ethyl-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 45
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-4-phenyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 46
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-4-phenyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 47
Dependent Claim
17 words
A member selected from the group consisting of 5-chloro-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 48
Dependent Claim
17 words
A member selected from the group consisting of 5-chloro-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 49
Dependent Claim
17 words
A member selected from the group consisting of 1-(1-methylethyl)-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 50
Dependent Claim
17 words
A member selected from the group consisting of 1-(1-methylethyl)-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 51
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 52
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 53
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-piperidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 54
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-piperidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 55
Dependent Claim
17 words
A member selected from the group consisting of 3-[4-(1-methyl-2-pyrrolidinyldeneamino)butylthio]indole and the therapeutically active acid addition salts thereof.
Claim 56
Dependent Claim
17 words
A member selected from the group consisting of 3-[4-(1-methyl-2-pyrrolidinyldeneamino)butylthio]indole and the therapeutically active acid addition salts thereof.
Claim 57
Dependent Claim
17 words
A member selected from the group consisting of 1-(2-methyl-2-propenyl)-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 58
Dependent Claim
17 words
A member selected from the group consisting of 1-(2-methyl-2-propenyl)-3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 59
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-1-propylindole and the therapeutically active acid addition salts thereof.
Claim 60
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]-1-propylindole and the therapeutically active acid addition salts thereof.
Claim 61
Dependent Claim
17 words
A member selected from the group consisting of 3-{2-[1-(2-propenyl)-2-pyrrolidinylideneamino]ethylthio}indole and the therapeutically active acid addition salts thereof.
Claim 62
Dependent Claim
17 words
A member selected from the group consisting of 3-{2-[1-(2-propenyl)-2-pyrrolidinylideneamino]ethylthio}indole and the therapeutically active acid addition salts thereof.
Claim 63
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-hexahydroazapinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 64
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-2-hexahydroazapinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 65
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-1,4,5,6-tetrahydropyrimidin-2-ylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 66
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-1,4,5,6-tetrahydropyrimidin-2-ylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 67
Dependent Claim
17 words
A member selected from the group consisting of 2-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 68
Dependent Claim
17 words
A member selected from the group consisting of 2-[2-(1-methyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 69
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-5-phenyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
Claim 70
Dependent Claim
17 words
A member selected from the group consisting of 3-[2-(1-methyl-5-phenyl-2-pyrrolidinylideneamino)ethylthio]indole and the therapeutically active acid addition salts thereof.
References Cited (Backward Citations)
US3285908A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-11-21 | 1981-05-23 | 1981-11-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-11-21 | 1985-05-23 | 1985-11-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-11-21 | 1989-05-23 | 1989-11-22 | $7700.00 | Window Closed / Lapsed |