WO2001087308B1 - Treatment of fibromyalgia and chronic fatigue syndrome - Google Patents

Treatment of fibromyalgia and chronic fatigue syndrome

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Publication number
WO2001087308B1
WO2001087308B1 PCT/US2001/010806 US0110806W WO0187308B1 WO 2001087308 B1 WO2001087308 B1 WO 2001087308B1 US 0110806 W US0110806 W US 0110806W WO 0187308 B1 WO0187308 B1 WO 0187308B1
Authority
WO
WIPO (PCT)
Prior art keywords
trans
octahydropyrimido
pharmaceutically acceptable
quinoline
day
Prior art date
Application number
PCT/US2001/010806
Other languages
French (fr)
Other versions
WO2001087308A1 (en
Inventor
David W Robertson
Robert B Mccall
Robert C Marshall
Original Assignee
Upjohn Co
David W Robertson
Robert B Mccall
Robert C Marshall
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.)
Filing date
Publication date
Priority to BR0110188-9A priority Critical patent/BR0110188A/en
Priority to NZ522115A priority patent/NZ522115A/en
Priority to KR1020027014073A priority patent/KR20020089510A/en
Priority to EP01928355A priority patent/EP1280530A1/en
Priority to US10/258,203 priority patent/US20030212085A1/en
Priority to MXPA02010410A priority patent/MXPA02010410A/en
Priority to AU2001255223A priority patent/AU2001255223B2/en
Priority to JP2001583776A priority patent/JP2004502651A/en
Application filed by Upjohn Co, David W Robertson, Robert B Mccall, Robert C Marshall filed Critical Upjohn Co
Priority to CA002404704A priority patent/CA2404704A1/en
Priority to AU5522301A priority patent/AU5522301A/en
Priority to PCT/US2001/016522 priority patent/WO2002083141A1/en
Publication of WO2001087308A1 publication Critical patent/WO2001087308A1/en
Publication of WO2001087308B1 publication Critical patent/WO2001087308B1/en
Priority to HK03106406.2A priority patent/HK1054190A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4748—Quinolines; Isoquinolines forming part of bridged ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Neurology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Indole Compounds (AREA)

Abstract

The present invention relates to the treatment of neuromuscular disorders and, more specifically, to the use of apomorphine, bromocriptine, pergolide, ropinirole, octahydropyrazolo[3,4-g]quinolines, and trans-(±)-substituted-5,5a,6,7,8,9-,9a,10-octahydropyrimido[4,5g]quinolines, and their pharmaceutically acceptable salts to treat, or to prepare a medicament for treating, symptoms of fibromyalgia syndrome and chronic fatigue syndrome.

Claims

AMENDED CLAIMS
[received by the International Bureau on 29 October 2001 (29 10 01), new claims 20-34 added, remaining claims unchanged (3 pages)]
20 The method of claim 10 wherein said octahydropyrazolo[3,4-g]quιnolιne is a trans- (±)tereoιsomer existing as a tautomeπc pair of the formula
Figure imgf000002_0001
and formula
Figure imgf000002_0002
wherein R is methyl, ethyl, n-propyl or allyl
21 The method of claim 20 wherein R is n-propyl
22 The method of claim 20 wherein said octahydropyrazolo[3,4-g]quιnohne is 4aS,8aS- 5-n-propyl-4.4a.5.6,7,8,8a.9-octahydro-lH(and 2H)-pyrazolo[3.4-g]quιnolιne or a pharmaceutically acceptable salt thereof
23 The method of claim 10 wherein said octahydropyrazolo[3 4-g]quιnolιne is quinpirole or a pharmaceutically acceptable salt thereof
24 The method of claim 10 wherein the effective amount of said octahydropyrazolo[3.4- gjquinohne by oral administration is from about 0 3 to about 60 mg/kg/day
25 The method of claim 1 wherein said trans-(±)-substιtuted-5.5a,6,7,8.9-.9a.l0- octahydropyπmιdo[4.5-g]quιnohne is a trans-(±) racemate of the formula
Figure imgf000002_0003
-19- or stereoisomer thereof of formula
Figure imgf000003_0001
or a pharmaceutically acceptable salt thereof, wherein: R is CI - C3 alkyl or allyl, Rl is NH2, NHR3. NR4 R5 and R2 is H, CH3, CI or Br wherein R3 is methyl, ethyl or n-propyl, CI - C3 alkyl-CO, phenyl-CO or substituted phenyl-CO wherein said substituents are 1 or 2 members of the group: CI. F, Br, CH3. C2 H5, CH3 O. C2 H5 O and CF3: R4 and R5 are individually methyl, ethyl or n-propyl.
26. The method of claim 25 wherein said trans-(±)-substituted-5,5a,6,7,8.9-,9a.l0- octahydropyrimido[4,5-g]quinoline is trans-(±)-2-amino-6-n-propyl-5,5a,6,7, 8,9,9a, 10- octahydropyrimido[4,5-g Jquinoline.
27. The method of claim 25 wherein said trans-(±)-substιtuted-5.5a,6,7,8.9-.9a,10- octahydropyrimido[4,5-g]quinoline is trans-(-)-2-amino-6-n-propyl-5,5a,6,7.8.9,9a, 10- octahydropyrimido[4,5-g]quinoline.
28. The method of claim 25 wherein said trans-(±)-substituted-5.5a,6,7.8.9-.9a.l0- octahydropyrimido[4,5-g]quinoline is trans-(-)-2-amino-6-n-propyl-5.5a,6,7,8,9.9a,10- octahydropyrimido[4.5-g]quinoline dihydrochloride.
29. The method of claim 25 wherein said trans-(±)-substimted-5.5a.6,7,8.9-,9a,10- octahydropyrimido[4,5-g]quinoline is quinelorane or a pharmaceutically acceptable salt thereof.
-20-
30. The method of claim 25 wherein the effective amount of said trans-(±)-substituted- 5,5a,6,7,8,9-,9a,10- octahydropyrimido[4,5-g]quinoline for oral administration is from about 0.3 to about 400 mcg/kg/day.
31. The method of claim 25 wherein the effective amount of said trans-(±)-substituted- 5,5a,6,7,8,9-,9a,10- octahydropyrimido[4,5-g]quinoline for parenteral administration is from about 0.75 to about 100 mcg/kg/day.
32. Use of a compound to prepare a medicament for treating symptoms of fibromyalgia syndrome and chronic fatigue syndrome wherein said compound selected from the group consisting of apomorphine, bromocriptine. pergolide. ropinirole, one of the octahydropyrazolo[3,4-g]quinolines. and one of the trans-(±)-substituted-5.5a.6.7,8,9-,9a,10- octahydropyrimido[4.5-g]quinolines. or a pharmaceutically acceptable salt of any said compound.
33. The use of the compound in claim 32 wherein the amount of apomorphine or its pharmaceutically acceptable salts is from about 0.25 to about 12 mg/patient/day, the amount of bromocriptine or its pharmaceutically acceptable salts is from about 2.5 to about 15 mg patient/day, the amount of pergolide or its pharmaceutically acceptable salts is from about 0.75 to about 5 mg/patient/day, the amount of ropinirole or its pharmaceutically acceptable salts is from about 0.25 to about 25 mg/patient/day, the amount of the octahydropyrazolo[3,4-g]quinoline or its pharmaceutically acceptable salts is from about 0.3 to about 60 mg/kg/day, and the amount of the trans-(±)-substituted-5.5a,6,7,8.9-.9a,10- octahydropyrimido[4,5-g]quinoline or its pharmaceutically acceptable salts is from about 0.3 to about 400 mcg/kg/day.
34. The use of the compounds disclosed herein for treating symptoms of fibromyalgia syndrome and chronic fatigue syndrome.
-21-
PCT/US2001/010806 2000-04-21 2001-04-17 Treatment of fibromyalgia and chronic fatigue syndrome WO2001087308A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
AU2001255223A AU2001255223B2 (en) 2000-04-21 2001-04-17 Treatment of fibromyalgia and chronic fatigue syndrome
KR1020027014073A KR20020089510A (en) 2000-04-21 2001-04-17 Treatment of Fibromyalgia and Chronic Fatigue Syndrome
EP01928355A EP1280530A1 (en) 2000-04-21 2001-04-17 Treatment of fibromyalgia and chronic fatigue syndrome
US10/258,203 US20030212085A1 (en) 2001-04-17 2001-04-17 Treatment of fibromyalgia and chronic fatigue syndrome
MXPA02010410A MXPA02010410A (en) 2000-04-21 2001-04-17 Treatment of fibromyalgia and chronic fatigue syndrome.
BR0110188-9A BR0110188A (en) 2000-04-21 2001-04-17 Selected compounds for the treatment of fibromyalgia and chronic fatigue syndromes
JP2001583776A JP2004502651A (en) 2000-04-21 2001-04-17 Treatment of fibromyalgia and chronic fatigue syndrome
NZ522115A NZ522115A (en) 2000-04-21 2001-04-17 Selected compounds for the treatment of fibromyalgia and chronic fatigue syndrome
CA002404704A CA2404704A1 (en) 2000-04-21 2001-04-17 Treatment of fibromyalgia and chronic fatigue syndrome
AU5522301A AU5522301A (en) 2000-04-21 2001-04-17 Treatment of fibromyalgia and chronic fatigue syndrome
PCT/US2001/016522 WO2002083141A1 (en) 2001-04-17 2001-07-11 Treatment of fibromyalgia and chronic fatigue syndrome
HK03106406.2A HK1054190A1 (en) 2000-04-21 2003-09-09 Treatment of fibromyalgia and chronic fatigue syndrome

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US19896000P 2000-04-21 2000-04-21
US60/198,960 2000-04-21

Publications (2)

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WO2001087308B1 true WO2001087308B1 (en) 2002-05-16

Family

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EP (1) EP1280530A1 (en)
JP (1) JP2004502651A (en)
KR (1) KR20020089510A (en)
CN (1) CN1418099A (en)
AU (2) AU5522301A (en)
BR (1) BR0110188A (en)
CA (1) CA2404704A1 (en)
HK (1) HK1054190A1 (en)
MX (1) MXPA02010410A (en)
NZ (1) NZ522115A (en)
WO (1) WO2001087308A1 (en)
ZA (1) ZA200208272B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6277875B1 (en) * 2000-07-17 2001-08-21 Andrew J. Holman Use of dopamine D2/D3 receptor agonists to treat fibromyalgia
US20100035886A1 (en) 2007-06-21 2010-02-11 Veroscience, Llc Parenteral formulations of dopamine agonists
US8741918B2 (en) * 2007-06-21 2014-06-03 Veroscience Llc Parenteral formulations of dopamine agonists
EP4009973A4 (en) * 2019-08-07 2023-08-23 Aclipse One, Inc. Pharmaceutical compositions of (6as)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5073555A (en) * 1988-04-04 1991-12-17 George D. McAdory Medicaments intended for combined use in the improvement of lymphocyte function to lower cholesterol levels
US5696128A (en) * 1994-07-07 1997-12-09 The Board Of Supervisors Of Louisiana University And Agricultural And Mechanical College Method of regulating immune function
IT1304904B1 (en) * 1998-09-11 2001-04-05 Eisai Co Ltd ANTICOLINESTERASIC DERIVATIVES FOR THE TREATMENT OF FUNCTIONAL AND / OR ORGANIC SYNDROME
ES2246485T3 (en) * 1999-07-01 2006-02-16 PHARMACIA & UPJOHN COMPANY LLC (S, S) -REBOXETINE TO TREAT INCONTINENCE.
DE19938823A1 (en) * 1999-08-19 2001-02-22 Boehringer Ingelheim Pharma Treatment of restless leg syndrome symptoms, using synergistic combination of alpha-2 agonist, preferably clonidine, and another neuro-psychic drug, e.g. pramipexol
DK1274430T3 (en) * 2000-04-21 2006-02-13 Pharmacia & Upjohn Co Llc Cabergoline for the treatment of fibromyalgia and chronic fatigue syndrome
US6277875B1 (en) * 2000-07-17 2001-08-21 Andrew J. Holman Use of dopamine D2/D3 receptor agonists to treat fibromyalgia

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Publication number Publication date
KR20020089510A (en) 2002-11-29
AU5522301A (en) 2001-11-26
AU2001255223B2 (en) 2004-10-21
WO2001087308A1 (en) 2001-11-22
BR0110188A (en) 2003-03-05
MXPA02010410A (en) 2003-04-25
ZA200208272B (en) 2004-01-26
NZ522115A (en) 2004-07-30
HK1054190A1 (en) 2003-11-21
CA2404704A1 (en) 2001-11-22
CN1418099A (en) 2003-05-14
JP2004502651A (en) 2004-01-29
EP1280530A1 (en) 2003-02-05

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