IL124320A - History - 1 arylsulfonyl - or - 1 aryl (thio) carbonyl - pyridazine, their preparation and pharmaceutical preparations containing them - Google Patents

History - 1 arylsulfonyl - or - 1 aryl (thio) carbonyl - pyridazine, their preparation and pharmaceutical preparations containing them

Info

Publication number: IL124320A
Authority: IL; Israel
Prior art keywords: diazo; hexahydro; compound; hexahydrophenanthrene; benzo
Prior art date: 1995-11-06

Application number

IL12432096A

Other languages

English (en)

Hebrew (he)

Other versions

IL124320A0 (en

Original Assignee

Ortho Mcneil Pharm Inc

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.)

1995-11-06

Filing date

1996-10-10

Publication date

2001-10-31

1996-10-10 Application filed by Ortho Mcneil Pharm Inc filed Critical Ortho Mcneil Pharm Inc

1998-12-06 Publication of IL124320A0 publication Critical patent/IL124320A0/xx

2001-10-31 Publication of IL124320A publication Critical patent/IL124320A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title description 12
125000000446 sulfanediyl group Chemical group *S* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 56
-1 cyano, carboxyl Chemical group 0.000 claims abstract description 18
229910052736 halogen Inorganic materials 0.000 claims abstract description 13
150000002367 halogens Chemical class 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
150000002431 hydrogen Chemical class 0.000 claims abstract description 6
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 18
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
229910052725 zinc Inorganic materials 0.000 claims description 6
239000011701 zinc Substances 0.000 claims description 6
239000012280 lithium aluminium hydride Substances 0.000 claims description 5
206010006187 Breast cancer Diseases 0.000 claims description 3
208000026310 Breast neoplasm Diseases 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
201000009273 Endometriosis Diseases 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
230000006698 induction Effects 0.000 claims description 2
230000009245 menopause Effects 0.000 claims description 2
230000035935 pregnancy Effects 0.000 claims description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 8
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
150000007857 hydrazones Chemical class 0.000 claims 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical group ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
239000000583 progesterone congener Substances 0.000 abstract description 6
125000001188 haloalkyl group Chemical group 0.000 abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 133
239000000203 mixture Substances 0.000 description 41
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
239000007787 solid Substances 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
229910052943 magnesium sulfate Inorganic materials 0.000 description 15
235000019341 magnesium sulphate Nutrition 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
239000000706 filtrate Substances 0.000 description 14
229910052794 bromium Inorganic materials 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
238000004440 column chromatography Methods 0.000 description 7
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
102000003998 progesterone receptors Human genes 0.000 description 7
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239000007858 starting material Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
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230000000694 effects Effects 0.000 description 6
QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 5
XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
230000027455 binding Effects 0.000 description 4
210000000988 bone and bone Anatomy 0.000 description 4
210000000481 breast Anatomy 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
230000035755 proliferation Effects 0.000 description 4
QFFCYTLOTYIJMR-XMGTWHOFSA-N promegestone Chemical compound C1CC2=CC(=O)CCC2=C2[C@@H]1[C@@H]1CC[C@@](C(=O)CC)(C)[C@@]1(C)CC2 QFFCYTLOTYIJMR-XMGTWHOFSA-N 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
238000010992 reflux Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
DMXOUYZZHVHEQR-UHFFFAOYSA-N 5-bromo-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=C1C=CC=C2Br DMXOUYZZHVHEQR-UHFFFAOYSA-N 0.000 description 3
DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
230000000708 anti-progestin effect Effects 0.000 description 3
239000003418 antiprogestin Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000013058 crude material Substances 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
229940104230 thymidine Drugs 0.000 description 3
AYNCWMIFKFADCZ-UHFFFAOYSA-N 2-bromo-3,4-dihydro-2h-naphthalen-1-one Chemical class C1=CC=C2C(=O)C(Br)CCC2=C1 AYNCWMIFKFADCZ-UHFFFAOYSA-N 0.000 description 2
VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 2
KWHUHTFXMNQHAA-UHFFFAOYSA-N 6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound O=C1CCCCC2=CC=CC=C12 KWHUHTFXMNQHAA-UHFFFAOYSA-N 0.000 description 2
YGVDCGFUUUJCDF-UHFFFAOYSA-N 7-bromo-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(Br)=CC=C21 YGVDCGFUUUJCDF-UHFFFAOYSA-N 0.000 description 2
108091003079 Bovine Serum Albumin Proteins 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
102220497176 Small vasohibin-binding protein_T47D_mutation Human genes 0.000 description 2
210000002449 bone cell Anatomy 0.000 description 2
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239000003610 charcoal Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012091 fetal bovine serum Substances 0.000 description 2
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
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125000000623 heterocyclic group Chemical group 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
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QPRMGHKASRLPJP-UHFFFAOYSA-N 12-(5-hydroxy-6-methylpiperidin-2-yl)dodecan-2-one Chemical compound CC1NC(CCCCCCCCCCC(C)=O)CCC1O QPRMGHKASRLPJP-UHFFFAOYSA-N 0.000 description 1
WZJLGICGNMAUFC-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-fluorene Chemical compound C12=CC=CC=C2CC2=C1CCCC2 WZJLGICGNMAUFC-UHFFFAOYSA-N 0.000 description 1
JUWKFPCTXSBEAD-UHFFFAOYSA-N 2,4,4a,5-tetrahydroindeno[1,2-c]pyridazin-3-one Chemical compound C1=CC=C2C3=NNC(=O)CC3CC2=C1 JUWKFPCTXSBEAD-UHFFFAOYSA-N 0.000 description 1
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GGHLXLVPNZMBQR-UHFFFAOYSA-N 3,5-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=CC(Cl)=C1 GGHLXLVPNZMBQR-UHFFFAOYSA-N 0.000 description 1
UVVYFYLSZIMKMC-UHFFFAOYSA-N 4-bromo-2,3-dihydroinden-1-one Chemical compound BrC1=CC=CC2=C1CCC2=O UVVYFYLSZIMKMC-UHFFFAOYSA-N 0.000 description 1
SRLHDEROUKFEMJ-UHFFFAOYSA-N 4-methyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(C)CCC(=O)C2=C1 SRLHDEROUKFEMJ-UHFFFAOYSA-N 0.000 description 1
SEQHEDQNODAFIU-UHFFFAOYSA-N 6-bromo-2,3-dihydroinden-1-one Chemical compound BrC1=CC=C2CCC(=O)C2=C1 SEQHEDQNODAFIU-UHFFFAOYSA-N 0.000 description 1
WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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229920002554 vinyl polymer Polymers 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
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/36—Benzo-cinnolines

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Endocrinology (AREA)
Physical Education & Sports Medicine (AREA)
Reproductive Health (AREA)
Gynecology & Obstetrics (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Diabetes (AREA)
Pregnancy & Childbirth (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

IL12432096A 1995-11-06 1996-10-10 History - 1 arylsulfonyl - or - 1 aryl (thio) carbonyl - pyridazine, their preparation and pharmaceutical preparations containing them IL124320A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US790095P	1995-11-06	1995-11-06
PCT/US1996/016227 WO1997017332A1 (en)	1995-11-06	1996-10-10	1-arylsulphonyl, aryl(thio)carbonyl pyridazino derivatives and methods of preparation

Publications (2)

Publication Number	Publication Date
IL124320A0 IL124320A0 (en)	1998-12-06
IL124320A true IL124320A (en)	2001-10-31

Family

ID=21728709

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12432096A IL124320A (en)	1995-11-06	1996-10-10	History - 1 arylsulfonyl - or - 1 aryl (thio) carbonyl - pyridazine, their preparation and pharmaceutical preparations containing them

Country Status (17)

Country	Link
JP (1)	JP2000501073A (zh)
KR (1)	KR100360614B1 (zh)
CN (1)	CN1110485C (zh)
AU (1)	AU704507B2 (zh)
BR (1)	BR9611407A (zh)
CZ (1)	CZ286789B6 (zh)
HU (1)	HU225162B1 (zh)
IL (1)	IL124320A (zh)
MX (1)	MX9803605A (zh)
NO (1)	NO310460B1 (zh)
NZ (1)	NZ319979A (zh)
PL (1)	PL185618B1 (zh)
RU (1)	RU2175969C2 (zh)
TW (1)	TW460467B (zh)
UA (1)	UA48989C2 (zh)
WO (1)	WO1997017332A1 (zh)
ZA (1)	ZA969298B (zh)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4816467A (en) *	1987-01-09	1989-03-28	Farmitalia Carlo Erba S.R.L	Heteroaryl 3-oxo-propanenitrile derivatives, pharmaceutical compositions and use
WO1989004306A1 (fr) *	1987-11-02	1989-05-18	Yoshitomi Pharmaceutical Industries, Ltd.	Composes de pyridazine fusionnes et leurs utilisations medicales
CA2116448A1 (en) *	1991-08-27	1993-03-04	Tohru Nakao	Fused pyridazine compound and pharmaceutical use thereof

1996
- 1996-10-10 CN CN96199481A patent/CN1110485C/zh not_active Expired - Fee Related
- 1996-10-10 UA UA98052267A patent/UA48989C2/uk unknown
- 1996-10-10 NZ NZ319979A patent/NZ319979A/xx unknown
- 1996-10-10 JP JP9518177A patent/JP2000501073A/ja not_active Ceased
- 1996-10-10 AU AU72637/96A patent/AU704507B2/en not_active Ceased
- 1996-10-10 PL PL96326669A patent/PL185618B1/pl not_active IP Right Cessation
- 1996-10-10 HU HU0201305A patent/HU225162B1/hu not_active IP Right Cessation
- 1996-10-10 IL IL12432096A patent/IL124320A/en not_active IP Right Cessation
- 1996-10-10 WO PCT/US1996/016227 patent/WO1997017332A1/en not_active Ceased
- 1996-10-10 BR BR9611407-0A patent/BR9611407A/pt not_active Application Discontinuation
- 1996-10-10 RU RU98110813/04A patent/RU2175969C2/ru not_active IP Right Cessation
- 1996-10-10 CZ CZ19981380A patent/CZ286789B6/cs not_active IP Right Cessation
- 1996-10-10 KR KR10-1998-0703345A patent/KR100360614B1/ko not_active Expired - Fee Related
- 1996-11-05 ZA ZA9609298A patent/ZA969298B/xx unknown
- 1996-11-25 TW TW085114479A patent/TW460467B/zh not_active IP Right Cessation
1998
- 1998-05-05 NO NO19982030A patent/NO310460B1/no unknown
- 1998-05-06 MX MX9803605A patent/MX9803605A/es not_active IP Right Cessation

Also Published As

Publication number	Publication date
NZ319979A (en)	1999-11-29
AU7263796A (en)	1997-05-29
HU225162B1 (en)	2006-07-28
CZ286789B6 (en)	2000-07-12
KR19990067340A (ko)	1999-08-16
PL185618B1 (pl)	2003-06-30
JP2000501073A (ja)	2000-02-02
AU704507B2 (en)	1999-04-22
NO982030L (no)	1998-06-23
CZ138098A3 (cs)	1998-09-16
CN1207091A (zh)	1999-02-03
WO1997017332A1 (en)	1997-05-15
NO982030D0 (no)	1998-05-05
HUP0201305A2 (hu)	2002-12-28
PL326669A1 (en)	1998-10-12
IL124320A0 (en)	1998-12-06
NO310460B1 (no)	2001-07-09
HUP0201305A3 (en)	2003-02-28
TW460467B (en)	2001-10-21
RU2175969C2 (ru)	2001-11-20
MX9803605A (es)	1998-09-30
UA48989C2 (uk)	2002-09-16
ZA969298B (en)	1998-05-05
BR9611407A (pt)	1999-12-28
KR100360614B1 (ko)	2003-06-02
CN1110485C (zh)	2003-06-04

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NZ249158A (en)	1996-02-27	N-sulphonyl-2-oxindole derivatives and pharmaceutical compositions
JPH0653736B2 (ja)	1994-07-20	新規な酸性インド−ル化合物
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Legal Events

Date	Code	Title	Description
2002-12-01	KB	Patent renewed
2011-06-30	MM9K	Patent not in force due to non-payment of renewal fees