CA2302396C - Allosteric adenosine receptor modulators - Google Patents
Allosteric adenosine receptor modulators Download PDFInfo
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- CA2302396C CA2302396C CA002302396A CA2302396A CA2302396C CA 2302396 C CA2302396 C CA 2302396C CA 002302396 A CA002302396 A CA 002302396A CA 2302396 A CA2302396 A CA 2302396A CA 2302396 C CA2302396 C CA 2302396C
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- treatment
- amino
- hydrogen
- compound
- lower alkyl
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- 108050000203 Adenosine receptors Proteins 0.000 title claims abstract description 46
- 102000009346 Adenosine receptors Human genes 0.000 title claims abstract description 46
- 230000003281 allosteric effect Effects 0.000 title abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 192
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims abstract description 65
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims abstract description 19
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- 239000001257 hydrogen Substances 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 150000002431 hydrogen Chemical group 0.000 claims description 61
- -1 amino, amino Chemical group 0.000 claims description 38
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- 125000003342 alkenyl group Chemical group 0.000 claims description 28
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- CQQSPRAGMLYQRC-UHFFFAOYSA-N (2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)-phenylmethanone Chemical compound NC=1SC=2CNCCC=2C=1C(=O)C1=CC=CC=C1 CQQSPRAGMLYQRC-UHFFFAOYSA-N 0.000 claims description 9
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- HFLMHMGIVXQGIB-UHFFFAOYSA-N (2-aminothiophen-3-yl)-(4-chlorophenyl)methanone Chemical compound S1C=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1N HFLMHMGIVXQGIB-UHFFFAOYSA-N 0.000 claims description 3
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- VAOQLVBIABOKRH-UHFFFAOYSA-N [2-amino-6-(2-phenylethyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-3-yl]-[3-(fluoromethyl)phenyl]methanone Chemical compound C1CC=2C(C(=O)C=3C=C(CF)C=CC=3)=C(N)SC=2CN1CCC1=CC=CC=C1 VAOQLVBIABOKRH-UHFFFAOYSA-N 0.000 claims description 2
- UMHNMWWFIDTLMU-UHFFFAOYSA-N [2-amino-6-(3-phenylpropyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CC=2C(C(=O)C=3C=CC(Cl)=CC=3)=C(N)SC=2CN1CCCC1=CC=CC=C1 UMHNMWWFIDTLMU-UHFFFAOYSA-N 0.000 claims description 2
- XSWIIAHQEAQTIA-UHFFFAOYSA-N [2-amino-6-(3-phenylpropyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-3-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound C1CC=2C(C(=O)C=3C=C(C=CC=3)C(F)(F)F)=C(N)SC=2CN1CCCC1=CC=CC=C1 XSWIIAHQEAQTIA-UHFFFAOYSA-N 0.000 claims description 2
- XQVYRFCAMRPJQW-UHFFFAOYSA-N [2-amino-6-(4-methylphenyl)sulfonyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-3-yl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(SC(N)=C2C(=O)C=3C=CC=CC=3)=C2CC1 XQVYRFCAMRPJQW-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003275 alpha amino acid group Chemical group 0.000 claims description 2
- MFBXKDKZGFIBNE-UHFFFAOYSA-N ethyl 2-[2-amino-3-(4-chlorobenzoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-6-yl]acetate Chemical compound C1N(CC(=O)OCC)CCC2=C1SC(N)=C2C(=O)C1=CC=C(Cl)C=C1 MFBXKDKZGFIBNE-UHFFFAOYSA-N 0.000 claims description 2
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- YECOLIOURFRXLE-UHFFFAOYSA-N (2-amino-6-benzyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-3-yl)-[3-(trifluoromethyl)phenyl]methanone Chemical compound C1CC=2C(C(=O)C=3C=C(C=CC=3)C(F)(F)F)=C(N)SC=2CN1CC1=CC=CC=C1 YECOLIOURFRXLE-UHFFFAOYSA-N 0.000 claims 1
- OMPLSIJAEKIZMC-UHFFFAOYSA-N (2-amino-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-3-yl)-phenylmethanone Chemical compound C1N(C)CCC2=C1SC(N)=C2C(=O)C1=CC=CC=C1 OMPLSIJAEKIZMC-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
Landscapes
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- Pharmacology & Pharmacy (AREA)
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- Public Health (AREA)
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- Endocrinology (AREA)
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- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/959,758 US5939432A (en) | 1997-10-29 | 1997-10-29 | Thiophenes useful for modulating the adenosine receptor |
| US08/959,758 | 1997-10-29 | ||
| US09/156,077 US6323214B1 (en) | 1997-10-29 | 1998-09-17 | Allosteric adenosine receptor modulators |
| US09/156,077 | 1998-09-17 | ||
| PCT/US1998/020333 WO1999021617A2 (en) | 1997-10-29 | 1998-09-30 | Allosteric adenosine receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2302396A1 CA2302396A1 (en) | 1999-05-06 |
| CA2302396C true CA2302396C (en) | 2002-06-04 |
Family
ID=25502368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002302396A Expired - Fee Related CA2302396C (en) | 1997-10-29 | 1998-09-30 | Allosteric adenosine receptor modulators |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US5939432A (OSRAM) |
| EP (1) | EP1025106B1 (OSRAM) |
| JP (2) | JP2003517429A (OSRAM) |
| AT (1) | ATE330959T1 (OSRAM) |
| AU (1) | AU9671798A (OSRAM) |
| CA (1) | CA2302396C (OSRAM) |
| WO (1) | WO1999021617A2 (OSRAM) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6727258B2 (en) * | 1997-10-29 | 2004-04-27 | King Pharmaceutical Research & Development, Inc. | Allosteric adenosine receptor modulators |
| DE19947154A1 (de) * | 1999-10-01 | 2001-10-04 | Bayer Ag | Substituierte 2-Thio-3,5-dicyano-4-aryl-6-aminopyridine und ihre Verwendung |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CH540247A (de) * | 1967-04-21 | 1973-09-28 | Ciba Geigy Ag | Verfahren zur Herstellung von heterocyclischen, Asthylendoppelbindungen enthaltenden Verbindungen |
| ES393101A1 (es) * | 1971-07-09 | 1974-05-16 | Made Labor Sa | Procedimiento para la preparacion de derivados de tieno- diazepina. |
| FI54312C (fi) * | 1972-05-09 | 1978-11-10 | Sumitomo Chemical Co | Foerfarande foer framstaellning av tieno-(2,3-d)pyrimidinderivat med avsoendring av urinsyra i urin utoekande |
| JPS5342400B2 (OSRAM) | 1973-05-30 | 1978-11-10 | ||
| PH30676A (en) | 1986-07-22 | 1997-09-16 | Boehringer Ingelhein Kg | Hetrazepine compounds which have useful pharmaceutical utility |
| CH677511A5 (OSRAM) * | 1988-10-12 | 1991-05-31 | Mefina Sa | |
| US5026698A (en) | 1988-11-02 | 1991-06-25 | Nissan Chemical Industries, Ltd. | Thienopyridine type mevalonolactones |
| EP0407955A1 (de) * | 1989-07-12 | 1991-01-16 | Boehringer Ingelheim Kg | Neue Hetrazepine mit PAF-antagonistischer Wirkung, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CA2120939A1 (en) * | 1991-10-11 | 1993-04-15 | Tetsuya Tahara | Therapeutic agent for osteoporosis and diazepine compound |
| JPH05345785A (ja) * | 1992-01-16 | 1993-12-27 | Yoshitomi Pharmaceut Ind Ltd | トリアゾロオキサゼピン化合物 |
| TW263498B (OSRAM) * | 1993-11-10 | 1995-11-21 | Takeda Pharm Industry Co Ltd | |
| JPH07304755A (ja) * | 1994-05-12 | 1995-11-21 | Yamanouchi Pharmaceut Co Ltd | 縮合ジアゼピン誘導体 |
| AU699354B2 (en) * | 1994-11-08 | 1998-12-03 | Takeda Chemical Industries Ltd. | Thienopyridine or thienopyrimidine derivatives useful as anti-inflammatory agents or in the treatment of osteoporosis |
| US5585538A (en) | 1995-03-08 | 1996-12-17 | Pioneer Hi-Bred International, Inc. | Hybrid maize plant & seed (3936) |
| JPH08337583A (ja) * | 1995-04-13 | 1996-12-24 | Takeda Chem Ind Ltd | 複素環化合物およびその製造法 |
| US5757486A (en) * | 1996-11-22 | 1998-05-26 | Eastman Kodak Company | Digital camera image sensor positioning apparatus including a non-coherent light interferometer |
-
1997
- 1997-10-29 US US08/959,758 patent/US5939432A/en not_active Expired - Lifetime
-
1998
- 1998-09-30 EP EP98950745A patent/EP1025106B1/en not_active Expired - Lifetime
- 1998-09-30 CA CA002302396A patent/CA2302396C/en not_active Expired - Fee Related
- 1998-09-30 AU AU96717/98A patent/AU9671798A/en not_active Abandoned
- 1998-09-30 WO PCT/US1998/020333 patent/WO1999021617A2/en not_active Ceased
- 1998-09-30 JP JP2000517772A patent/JP2003517429A/ja active Pending
- 1998-09-30 AT AT98950745T patent/ATE330959T1/de not_active IP Right Cessation
-
1999
- 1999-05-07 US US09/307,225 patent/US6177444B1/en not_active Expired - Fee Related
- 1999-05-07 US US09/307,286 patent/US6194449B1/en not_active Expired - Fee Related
-
2004
- 2004-08-02 JP JP2004225107A patent/JP2005002129A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2302396A1 (en) | 1999-05-06 |
| ATE330959T1 (de) | 2006-07-15 |
| JP2005002129A (ja) | 2005-01-06 |
| US6194449B1 (en) | 2001-02-27 |
| WO1999021617A3 (en) | 1999-07-29 |
| EP1025106A2 (en) | 2000-08-09 |
| US6177444B1 (en) | 2001-01-23 |
| EP1025106B1 (en) | 2006-06-21 |
| JP2003517429A (ja) | 2003-05-27 |
| AU9671798A (en) | 1999-05-17 |
| WO1999021617A2 (en) | 1999-05-06 |
| WO1999021617B1 (en) | 1999-09-10 |
| US5939432A (en) | 1999-08-17 |
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