FI59597C - Nytt foerfarande foer framstaellning av 5-oxo-10-hydroxi-1,2,3,4-tetrahydro-5h-bensopyranopyridiner - Google Patents

Nytt foerfarande foer framstaellning av 5-oxo-10-hydroxi-1,2,3,4-tetrahydro-5h-bensopyranopyridiner Download PDF

Info

Publication number: FI59597C
Authority: FI; Finland
Prior art keywords: oxo; tetrahydro; formula; mixture; stirred
Prior art date: 1972-10-16

Application number

FI3019/73A

Other languages

English (en)

Finnish (fi)

Other versions

FI59597B (fi

Inventor

Howard Bernard Wright

Bruce Wayne Horrom

Original Assignee

Abbott Lab

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.)

1972-10-16

Filing date

1973-09-27

Publication date

1981-09-10

1973-09-27 Application filed by Abbott Lab filed Critical Abbott Lab

1981-01-16 Priority to FI810118A priority Critical patent/FI810118L/fi

1981-05-29 Application granted granted Critical

1981-05-29 Publication of FI59597B publication Critical patent/FI59597B/fi

1981-09-10 Publication of FI59597C publication Critical patent/FI59597C/fi

Links

AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 18
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 18
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 13
229940098779 methanesulfonic acid Drugs 0.000 claims description 11
238000000034 method Methods 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000003377 acid catalyst Substances 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
-1 4-fluorophenyl-1-methylbutyl Chemical group 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
239000007787 solid Substances 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 6
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
FULCMGRANBCDAK-UHFFFAOYSA-N 10h-chromeno[3,2-b]pyridine Chemical class C1=CN=C2CC3=CC=CC=C3OC2=C1 FULCMGRANBCDAK-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 3
IRMPFYJSHJGOPE-UHFFFAOYSA-N olivetol Chemical compound CCCCCC1=CC(O)=CC(O)=C1 IRMPFYJSHJGOPE-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
238000003763 carbonization Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000376 reactant Substances 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
LFAMTYOOZUPASP-UHFFFAOYSA-N 5-(3-methyloctan-2-yl)benzene-1,3-diol Chemical compound CCCCCC(C)C(C)C1=CC(O)=CC(O)=C1 LFAMTYOOZUPASP-UHFFFAOYSA-N 0.000 description 1
RKCBNCOFPKXLIQ-UHFFFAOYSA-N 5-propan-2-ylbenzene-1,3-diol Chemical compound CC(C)C1=CC(O)=CC(O)=C1 RKCBNCOFPKXLIQ-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
101001065065 Aspergillus awamori Feruloyl esterase A Proteins 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000004791 alkyl magnesium halides Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000013058 crude material Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
UQOMEAWPKSISII-UHFFFAOYSA-N ethyl 1-benzyl-3-oxopiperidine-4-carboxylate;hydron;chloride Chemical compound Cl.C1C(=O)C(C(=O)OCC)CCN1CC1=CC=CC=C1 UQOMEAWPKSISII-UHFFFAOYSA-N 0.000 description 1
OEEFUPHRORUMAR-UHFFFAOYSA-N ethyl 3-oxo-1-azabicyclo[2.2.2]octane-2-carboxylate;hydrochloride Chemical compound Cl.C1CC2CCN1C(C(=O)OCC)C2=O OEEFUPHRORUMAR-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Furan Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

FI3019/73A 1972-10-16 1973-09-27 Nytt foerfarande foer framstaellning av 5-oxo-10-hydroxi-1,2,3,4-tetrahydro-5h-bensopyranopyridiner FI59597C (fi)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
FI810118A FI810118L (fi)	1972-10-16	1981-01-16	Foerfarande foer framstaellning av terapeutiskt anvaendbara alkylfenylbensopyranopyridiner

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US29813272A	1972-10-16	1972-10-16
US29813272		1972-10-16
US367027A US3915996A (en)	1972-10-16	1973-06-08	Process for making benzopyrans
US36702773		1973-06-08

Publications (2)

Publication Number	Publication Date
FI59597B FI59597B (fi)	1981-05-29
FI59597C true FI59597C (fi)	1981-09-10

Family

ID=26970493

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI3019/73A FI59597C (fi)	1972-10-16	1973-09-27	Nytt foerfarande foer framstaellning av 5-oxo-10-hydroxi-1,2,3,4-tetrahydro-5h-bensopyranopyridiner

Country Status (12)

Country	Link
US (1)	US3915996A (th)
JP (1)	JPS4972259A (th)
CA (1)	CA992080A (th)
CH (1)	CH591468A5 (th)
DE (1)	DE2351734A1 (th)
DK (1)	DK143029C (th)
FI (1)	FI59597C (th)
FR (1)	FR2202887B1 (th)
GB (1)	GB1438833A (th)
NL (1)	NL7313595A (th)
NO (1)	NO141089C (th)
PH (1)	PH10496A (th)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3983110A (en) *	1974-12-19	1976-09-28	Warner-Lambert Company	Substituted benzopyranopyridine
US4137232A (en) *	1978-04-19	1979-01-30	Abbott Laboratories	2,8-Disubstituted-10-hydroxy-5,5-dimethyl-1,2,3,4-tetrahydro-5H -[1]benzopyrano[4,3-c]pyridine
EP0161218B1 (de) *	1984-05-10	1991-06-26	Ciba-Geigy Ag	Benzo-(pyrano und thiopyrano)-pyridine
US4666916A (en) *	1985-11-08	1987-05-19	Ciba-Geigy Corporation	Hexahydro-(1)-benzo-(pyrano and thiopyrano) (4,3-C)pyridines, useful as serotin-2 blocking agents
ATE277921T1 (de) *	1998-05-04	2004-10-15	Univ Connecticut	Selektiv auf den cb2-rezeptor wirkende cannabinoide
CA2340445A1 (en) *	1998-05-04	1999-11-11	The University Of Connecticut	Novel analgesic and immunomodulatory cannabinoids
US7589220B2 (en) *	1998-06-09	2009-09-15	University Of Connecticut	Inhibitors of the anandamide transporter
US7897598B2 (en) *	1998-06-09	2011-03-01	Alexandros Makriyannis	Inhibitors of the anandamide transporter
US7161016B1 (en)	1998-11-24	2007-01-09	University Of Connecticut	Cannabimimetic lipid amides as useful medications
US7276613B1 (en)	1998-11-24	2007-10-02	University Of Connecticut	Retro-anandamides, high affinity and stability cannabinoid receptor ligands
US6943266B1 (en) *	1999-10-18	2005-09-13	University Of Connecticut	Bicyclic cannabinoid agonists for the cannabinoid receptor
CA2387764A1 (en)	1999-10-18	2001-04-26	University Of Connecticut	Peripheral cannabinoid receptor (cb2) selective ligands
US8084467B2 (en) *	1999-10-18	2011-12-27	University Of Connecticut	Pyrazole derivatives as cannabinoid receptor antagonists
US7741365B2 (en) *	1999-10-18	2010-06-22	University Of Connecticut	Peripheral cannabinoid receptor (CB2) selective ligands
US6900236B1 (en)	1999-10-18	2005-05-31	University Of Connecticut	Cannabimimetic indole derivatives
US7119108B1 (en)	1999-10-18	2006-10-10	University Of Connecticut	Pyrazole derivatives as cannabinoid receptor antagonists
US7393842B2 (en) *	2001-08-31	2008-07-01	University Of Connecticut	Pyrazole analogs acting on cannabinoid receptors
EP1361876A4 (en) *	2001-01-26	2004-03-31	Univ Connecticut	NEW CANNABIMIMETIC LIGANDS
DE60237431D1 (de)	2001-01-29	2010-10-07	Univ Connecticut	Rezeptor-selektive cannabimimetische aminoalkylindole
JP4312594B2 (ja) *	2001-07-13	2009-08-12	ユニバーシティオブコネチカット	新規な二環式及び三環式カンナビノイド
US7666867B2 (en) *	2001-10-26	2010-02-23	University Of Connecticut	Heteroindanes: a new class of potent cannabimimetic ligands
AU2003265663A1 (en)	2002-08-23	2004-03-11	University Of Connecticut	Keto cannabinoids with therapeutic indications
CN1809552A (zh) *	2003-05-20	2006-07-26	田纳西大学研究基金会	大麻素衍生物、其制备方法和用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2419935A (en) *	1941-07-09	1947-05-06	Adams Roger	Marihuana active compounds
US2419934A (en) *	1941-07-09	1947-05-06	Adams Roger	Optically active tetrahydrodibenzopyrans having marihuana activity and process for making same
US3639426A (en) *	1970-01-08	1972-02-01	Little Inc A	4-oxo-9-hydroxy-7-(3-methyl-2-octyl)-1 2 3 4-tetrahydrocyclopenta(c)(1)benzopyran

1973
- 1973-06-08 US US367027A patent/US3915996A/en not_active Expired - Lifetime
- 1973-09-13 CA CA180,946A patent/CA992080A/en not_active Expired
- 1973-09-21 GB GB4447873A patent/GB1438833A/en not_active Expired
- 1973-09-27 FI FI3019/73A patent/FI59597C/fi active
- 1973-10-03 NL NL7313595A patent/NL7313595A/xx not_active Application Discontinuation
- 1973-10-04 PH PH15087A patent/PH10496A/en unknown
- 1973-10-09 JP JP48112902A patent/JPS4972259A/ja active Pending
- 1973-10-15 FR FR7336784A patent/FR2202887B1/fr not_active Expired
- 1973-10-15 DE DE19732351734 patent/DE2351734A1/de not_active Withdrawn
- 1973-10-15 NO NO4000/73A patent/NO141089C/no unknown
- 1973-10-15 DK DK557573A patent/DK143029C/da not_active IP Right Cessation
- 1973-10-16 CH CH1462673A patent/CH591468A5/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU6066373A (en)	1975-03-27
CH591468A5 (th)	1977-09-15
JPS4972259A (th)	1974-07-12
NL7313595A (th)	1974-04-18
NO141089C (no)	1980-01-09
GB1438833A (en)	1976-06-09
FR2202887A1 (th)	1974-05-10
US3915996A (en)	1975-10-28
DK143029C (da)	1981-10-26
DE2351734A1 (de)	1974-04-18
PH10496A (en)	1977-05-17
CA992080A (en)	1976-06-29
FR2202887B1 (th)	1978-05-26
DK143029B (da)	1981-03-16
NO141089B (no)	1979-10-01
FI59597B (fi)	1981-05-29

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