ZA200105253B - Substituted 2-arylimino heterocycles and compositions containing them for use as progesterone receptor binding agents. - Google Patents
Substituted 2-arylimino heterocycles and compositions containing them for use as progesterone receptor binding agents. Download PDFInfo
- Publication number
- ZA200105253B ZA200105253B ZA200105253A ZA200105253A ZA200105253B ZA 200105253 B ZA200105253 B ZA 200105253B ZA 200105253 A ZA200105253 A ZA 200105253A ZA 200105253 A ZA200105253 A ZA 200105253A ZA 200105253 B ZA200105253 B ZA 200105253B
- Authority
- ZA
- South Africa
- Prior art keywords
- carbons
- alkyl
- group
- halogen
- methyl
- Prior art date
Links
- 102000003998 progesterone receptors Human genes 0.000 title description 10
- 108090000468 progesterone receptors Proteins 0.000 title description 10
- 239000000203 mixture Substances 0.000 title description 9
- 239000011230 binding agent Substances 0.000 title description 3
- 125000001424 substituent group Chemical group 0.000 claims description 122
- 125000000217 alkyl group Chemical group 0.000 claims description 116
- 229910052736 halogen Inorganic materials 0.000 claims description 82
- 150000002367 halogens Chemical class 0.000 claims description 82
- 238000011282 treatment Methods 0.000 claims description 62
- 125000003342 alkenyl group Chemical group 0.000 claims description 53
- 229910052760 oxygen Inorganic materials 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 230000002265 prevention Effects 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 8
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 8
- 230000035935 pregnancy Effects 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical group C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 6
- 230000006698 induction Effects 0.000 claims description 6
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 6
- 210000000287 oocyte Anatomy 0.000 claims description 6
- 230000002611 ovarian Effects 0.000 claims description 6
- 230000001568 sexual effect Effects 0.000 claims description 6
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical group C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 230000009245 menopause Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000003003 spiro group Chemical group 0.000 claims description 5
- 206010003694 Atrophy Diseases 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010013908 Dysfunctional uterine bleeding Diseases 0.000 claims description 4
- 201000009273 Endometriosis Diseases 0.000 claims description 4
- 206010027514 Metrorrhagia Diseases 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 4
- 230000037444 atrophy Effects 0.000 claims description 4
- 210000000988 bone and bone Anatomy 0.000 claims description 4
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 230000002357 endometrial effect Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000006872 improvement Effects 0.000 claims description 4
- 230000000938 luteal effect Effects 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 208000010392 Bone Fractures Diseases 0.000 claims description 3
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 3
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 3
- 206010017076 Fracture Diseases 0.000 claims description 3
- 206010020112 Hirsutism Diseases 0.000 claims description 3
- 206010020571 Hyperaldosteronism Diseases 0.000 claims description 3
- 208000029725 Metabolic bone disease Diseases 0.000 claims description 3
- 206010049088 Osteopenia Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 201000009916 Postpartum depression Diseases 0.000 claims description 3
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 208000002495 Uterine Neoplasms Diseases 0.000 claims description 3
- 206010046798 Uterine leiomyoma Diseases 0.000 claims description 3
- 206010047791 Vulvovaginal dryness Diseases 0.000 claims description 3
- 239000004015 abortifacient agent Substances 0.000 claims description 3
- 231100000641 abortifacient agent Toxicity 0.000 claims description 3
- 230000030120 acrosome reaction Effects 0.000 claims description 3
- 230000033228 biological regulation Effects 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 230000000939 contragestive effect Effects 0.000 claims description 3
- 230000007812 deficiency Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000002296 eclampsia Diseases 0.000 claims description 3
- 230000004720 fertilization Effects 0.000 claims description 3
- 210000004392 genitalia Anatomy 0.000 claims description 3
- 230000003779 hair growth Effects 0.000 claims description 3
- 230000035876 healing Effects 0.000 claims description 3
- 230000036737 immune function Effects 0.000 claims description 3
- 238000002513 implantation Methods 0.000 claims description 3
- 238000000338 in vitro Methods 0.000 claims description 3
- 208000000509 infertility Diseases 0.000 claims description 3
- 230000036512 infertility Effects 0.000 claims description 3
- 231100000535 infertility Toxicity 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 201000010260 leiomyoma Diseases 0.000 claims description 3
- 239000002583 male contraceptive agent Substances 0.000 claims description 3
- 230000035800 maturation Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000007659 motor function Effects 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 230000011164 ossification Effects 0.000 claims description 3
- 201000011461 pre-eclampsia Diseases 0.000 claims description 3
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 230000008439 repair process Effects 0.000 claims description 3
- 230000037152 sensory function Effects 0.000 claims description 3
- 230000006403 short-term memory Effects 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 208000022925 sleep disturbance Diseases 0.000 claims description 3
- 230000021595 spermatogenesis Effects 0.000 claims description 3
- 230000007704 transition Effects 0.000 claims description 3
- 206010046766 uterine cancer Diseases 0.000 claims description 3
- 230000003313 weakening effect Effects 0.000 claims description 3
- YPHLQPXFMAHFFG-QGZVFWFLSA-N (4r)-n-(2-methyl-4-nitrophenyl)-3-(2-methylpropyl)-4-propan-2-yl-1,3-thiazinan-2-imine Chemical compound CC(C)CN1[C@@H](C(C)C)CCSC1=NC1=CC=C([N+]([O-])=O)C=C1C YPHLQPXFMAHFFG-QGZVFWFLSA-N 0.000 claims description 2
- SAPGYHFNQUNNPL-INIZCTEOSA-N (4s)-n-(2-methyl-4-nitrophenyl)-3,4-bis(2-methylpropyl)-1,3-thiazolidin-2-imine Chemical compound CC(C)CN1[C@@H](CC(C)C)CSC1=NC1=CC=C([N+]([O-])=O)C=C1C SAPGYHFNQUNNPL-INIZCTEOSA-N 0.000 claims description 2
- GUJBOMXEFNBUJR-UHFFFAOYSA-N 1-cyclohexyl-n-(2-methyl-4-nitrophenyl)-3-thia-1-azaspiro[4.4]nonan-2-imine Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N=C1N(C2CCCCC2)C2(CCCC2)CS1 GUJBOMXEFNBUJR-UHFFFAOYSA-N 0.000 claims description 2
- ZXIOHKLKWRDUKK-UHFFFAOYSA-N 1-cyclopentyl-n-(2,3-dimethyl-4-nitrophenyl)-3-thia-1-azaspiro[4.4]nonan-2-imine Chemical compound CC1=C(C)C([N+]([O-])=O)=CC=C1N=C1N(C2CCCC2)C2(CCCC2)CS1 ZXIOHKLKWRDUKK-UHFFFAOYSA-N 0.000 claims description 2
- SKACZZQWCFGTOO-UHFFFAOYSA-N 1-cyclopentyl-n-(2-methyl-4-nitrophenyl)-3-thia-1-azaspiro[4.4]nonan-2-imine Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N=C1N(C2CCCC2)C2(CCCC2)CS1 SKACZZQWCFGTOO-UHFFFAOYSA-N 0.000 claims description 2
- HFPKXEQJCQBPIP-UHFFFAOYSA-N 2-(3-methyl-4-nitrophenyl)imino-3-(2-methylpropyl)-1,3-thiazolidin-4-one Chemical compound CC(C)CN1C(=O)CSC1=NC1=CC=C([N+]([O-])=O)C(C)=C1 HFPKXEQJCQBPIP-UHFFFAOYSA-N 0.000 claims description 2
- NTUNKNYPEADWOY-UHFFFAOYSA-N 3-(1-cyclohexylethyl)-2-(2-methyl-4-nitrophenyl)imino-1,3-thiazolidin-4-one Chemical compound O=C1CSC(=NC=2C(=CC(=CC=2)[N+]([O-])=O)C)N1C(C)C1CCCCC1 NTUNKNYPEADWOY-UHFFFAOYSA-N 0.000 claims description 2
- BBFCJFHXZWIERU-UHFFFAOYSA-N 3-(2-methylbutyl)-2-(2-methyl-4-nitrophenyl)imino-1,3-thiazolidin-4-one Chemical compound CCC(C)CN1C(=O)CSC1=NC1=CC=C([N+]([O-])=O)C=C1C BBFCJFHXZWIERU-UHFFFAOYSA-N 0.000 claims description 2
- NILBFKSUWMNUJQ-UHFFFAOYSA-N 3-(2-methylbutyl)-2-(3-methyl-4-nitrophenyl)imino-1,3-thiazolidin-4-one Chemical compound CCC(C)CN1C(=O)CSC1=NC1=CC=C([N+]([O-])=O)C(C)=C1 NILBFKSUWMNUJQ-UHFFFAOYSA-N 0.000 claims description 2
- CTBQPWNZCJSWFX-UHFFFAOYSA-N 3-benzyl-2-(2-methyl-4-nitrophenyl)imino-1,3-thiazolidin-4-one Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N=C1N(CC=2C=CC=CC=2)C(=O)CS1 CTBQPWNZCJSWFX-UHFFFAOYSA-N 0.000 claims description 2
- KVVSYXLENURPHI-UHFFFAOYSA-N 3-methyl-4-[(1-pentan-3-yl-3-thia-1-azaspiro[4.4]nonan-2-ylidene)amino]benzonitrile Chemical compound CCC(CC)N1C(=NC=2C(=CC(=CC=2)C#N)C)SCC11CCCC1 KVVSYXLENURPHI-UHFFFAOYSA-N 0.000 claims description 2
- UUTFVHMCJDEXCQ-UHFFFAOYSA-N 3-methyl-4-[[1-(2-methylpropyl)-3-thia-1-azaspiro[4.4]nonan-2-ylidene]amino]benzonitrile Chemical compound CC(C)CN1C(=NC=2C(=CC(=CC=2)C#N)C)SCC11CCCC1 UUTFVHMCJDEXCQ-UHFFFAOYSA-N 0.000 claims description 2
- PTZJSANBUKXPHQ-UHFFFAOYSA-N 4-[(1-cyclopentyl-3-thia-1-azaspiro[4.4]nonan-2-ylidene)amino]-2,3-dimethylbenzonitrile Chemical compound C1=CC(C#N)=C(C)C(C)=C1N=C1N(C2CCCC2)C2(CCCC2)CS1 PTZJSANBUKXPHQ-UHFFFAOYSA-N 0.000 claims description 2
- FSKNZNKSZYBXPI-UHFFFAOYSA-N 4-[(1-cyclopentyl-3-thia-1-azaspiro[4.4]nonan-2-ylidene)amino]-3-ethylbenzonitrile Chemical compound CCC1=CC(C#N)=CC=C1N=C1N(C2CCCC2)C2(CCCC2)CS1 FSKNZNKSZYBXPI-UHFFFAOYSA-N 0.000 claims description 2
- PVDZPPKCOPAFGO-UHFFFAOYSA-N 4-[(1-cyclopentyl-3-thia-1-azaspiro[4.4]nonan-2-ylidene)amino]-3-methylbenzonitrile Chemical compound CC1=CC(C#N)=CC=C1N=C1N(C2CCCC2)C2(CCCC2)CS1 PVDZPPKCOPAFGO-UHFFFAOYSA-N 0.000 claims description 2
- NVIGNWXZKCVZJJ-UHFFFAOYSA-N 4-[[1-(2-methylpropyl)-3-thia-1-azaspiro[4.4]nonan-2-ylidene]amino]naphthalene-1-carbonitrile Chemical compound CC(C)CN1C(=NC=2C3=CC=CC=C3C(C#N)=CC=2)SCC11CCCC1 NVIGNWXZKCVZJJ-UHFFFAOYSA-N 0.000 claims description 2
- FKUVXSVSAXJFLO-UHFFFAOYSA-N 5-methyl-2-(2-methyl-4-nitrophenyl)imino-3-(2-methylpropyl)-1,3-thiazolidin-4-one Chemical compound CC(C)CN1C(=O)C(C)SC1=NC1=CC=C([N+]([O-])=O)C=C1C FKUVXSVSAXJFLO-UHFFFAOYSA-N 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- MMEBSAQPQQJAIK-UHFFFAOYSA-N n-(2-methyl-4-nitrophenyl)-1-prop-2-enyl-3-thia-1-azaspiro[4.4]nonan-2-imine Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N=C1N(CC=C)C2(CCCC2)CS1 MMEBSAQPQQJAIK-UHFFFAOYSA-N 0.000 claims description 2
- YSGWKTKRMLCHHI-UHFFFAOYSA-N n-(2-methyl-4-nitrophenyl)-1-propan-2-yl-3-thia-1-azaspiro[4.4]nonan-2-imine Chemical compound CC(C)N1C(=NC=2C(=CC(=CC=2)[N+]([O-])=O)C)SCC11CCCC1 YSGWKTKRMLCHHI-UHFFFAOYSA-N 0.000 claims description 2
- 201000004228 ovarian endometrial cancer Diseases 0.000 claims description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 2
- CWJUYADYSRQAAM-KRWDZBQOSA-N (4s)-3-cyclopentyl-n-(2-methyl-4-nitrophenyl)-4-(2-methylpropyl)-1,3-thiazolidin-2-imine Chemical compound C([C@@H](N1C2CCCC2)CC(C)C)SC1=NC1=CC=C([N+]([O-])=O)C=C1C CWJUYADYSRQAAM-KRWDZBQOSA-N 0.000 claims 1
- FZEDMJHMSJCXTA-UHFFFAOYSA-N 1-cyclohexyl-n-(2-methyl-4-nitrophenyl)-3-oxa-1-azaspiro[4.4]nonan-2-imine Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N=C1N(C2CCCCC2)C2(CCCC2)CO1 FZEDMJHMSJCXTA-UHFFFAOYSA-N 0.000 claims 1
- RLMBQZJBUAGYTF-UHFFFAOYSA-N 1-cyclopentyl-n-(2-methyl-4-nitrophenyl)-3-oxa-1-azaspiro[4.4]nonan-2-imine Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N=C1N(C2CCCC2)C2(CCCC2)CO1 RLMBQZJBUAGYTF-UHFFFAOYSA-N 0.000 claims 1
- FQZUPLVJTIZVCM-UHFFFAOYSA-N 2,3-dimethyl-4-[[1-(2-methylpropyl)-3-thia-1-azaspiro[4.4]nonan-2-ylidene]amino]benzonitrile Chemical compound CC(C)CN1C(=NC=2C(=C(C)C(C#N)=CC=2)C)SCC11CCCC1 FQZUPLVJTIZVCM-UHFFFAOYSA-N 0.000 claims 1
- NVMBMSKJWFEVDQ-UHFFFAOYSA-N 3-benzyl-2-(3-methyl-4-nitrophenyl)imino-1,3-thiazolidin-4-one Chemical compound C1=C([N+]([O-])=O)C(C)=CC(N=C2N(C(=O)CS2)CC=2C=CC=CC=2)=C1 NVMBMSKJWFEVDQ-UHFFFAOYSA-N 0.000 claims 1
- 230000036651 mood Effects 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- -1 Li* Na* or K*) Chemical class 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 6
- 238000002560 therapeutic procedure Methods 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 230000036541 health Effects 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000583 progesterone congener Substances 0.000 description 4
- 239000003765 sweetening agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010014733 Endometrial cancer Diseases 0.000 description 3
- 206010014759 Endometrial neoplasm Diseases 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 229940011871 estrogen Drugs 0.000 description 3
- 239000000262 estrogen Substances 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 235000003599 food sweetener Nutrition 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229940057995 liquid paraffin Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical class NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 235000006491 Acacia senegal Nutrition 0.000 description 2
- 235000003911 Arachis Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 206010060800 Hot flush Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010027940 Mood altered Diseases 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229930003316 Vitamin D Natural products 0.000 description 2
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000708 anti-progestin effect Effects 0.000 description 2
- 239000003418 antiprogestin Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000009164 estrogen replacement therapy Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000002657 hormone replacement therapy Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- 230000007510 mood change Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 230000000306 recurrent effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 235000019166 vitamin D Nutrition 0.000 description 2
- 239000011710 vitamin D Substances 0.000 description 2
- 150000003710 vitamin D derivatives Chemical class 0.000 description 2
- 229940046008 vitamin d Drugs 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- XQFGVGNRDPFKFJ-UHFFFAOYSA-N 1,2,3,5,6,7-hexahydropyrrolo[1,2-b]pyridazine Chemical compound N1CCC=C2CCCN21 XQFGVGNRDPFKFJ-UHFFFAOYSA-N 0.000 description 1
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical class O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- LAUYJPDPFRHBEN-UHFFFAOYSA-N 1-cyclopentyl-n-(3-methyl-4-nitrophenyl)-3-thia-1-azaspiro[4.4]nonan-2-imine Chemical compound C1=C([N+]([O-])=O)C(C)=CC(N=C2N(C3(CCCC3)CS2)C2CCCC2)=C1 LAUYJPDPFRHBEN-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- UOBAUMNLOZCUIS-UHFFFAOYSA-N 2-(2-methyl-4-nitrophenyl)imino-3-(2-methylpropyl)-1,3-thiazolidin-4-one Chemical compound CC(C)CN1C(=O)CSC1=NC1=CC=C([N+]([O-])=O)C=C1C UOBAUMNLOZCUIS-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- RXRPDLFWZHYJNK-UHFFFAOYSA-N 3-(1-cyclohexylethyl)-2-(3-methyl-4-nitrophenyl)imino-1,3-thiazolidin-4-one Chemical compound O=C1CSC(=NC=2C=C(C)C(=CC=2)[N+]([O-])=O)N1C(C)C1CCCCC1 RXRPDLFWZHYJNK-UHFFFAOYSA-N 0.000 description 1
- DFXJYOMSKJQBOP-UHFFFAOYSA-N 3-(2-ethylbutyl)-2-(2-methyl-4-nitrophenyl)imino-1,3-thiazolidin-4-one Chemical compound CCC(CC)CN1C(=O)CSC1=NC1=CC=C([N+]([O-])=O)C=C1C DFXJYOMSKJQBOP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LNZFJCMFKULQCV-UHFFFAOYSA-N 4,4-dimethyl-n-(2-methyl-4-nitrophenyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-imine Chemical compound O1CC(C)(C)N(CC(C)C)C1=NC1=CC=C([N+]([O-])=O)C=C1C LNZFJCMFKULQCV-UHFFFAOYSA-N 0.000 description 1
- ZYOMURLCAFCJCI-UHFFFAOYSA-N 4-[(1-cyclopentyl-3-oxa-1-azaspiro[4.4]nonan-2-ylidene)amino]-3-ethylbenzonitrile Chemical compound CCC1=CC(C#N)=CC=C1N=C1N(C2CCCC2)C2(CCCC2)CO1 ZYOMURLCAFCJCI-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- KKPRNPXQWRZYPB-UHFFFAOYSA-N 5-methylidene-2-(2-methyl-4-nitrophenyl)imino-3-(2-methylpropyl)-1,3-thiazolidin-4-one Chemical compound S1C(=C)C(=O)N(CC(C)C)C1=NC1=CC=C([N+]([O-])=O)C=C1C KKPRNPXQWRZYPB-UHFFFAOYSA-N 0.000 description 1
- 208000037853 Abnormal uterine bleeding Diseases 0.000 description 1
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000022211 Arteriovenous Malformations Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229940122361 Bisphosphonate Drugs 0.000 description 1
- 102000055006 Calcitonin Human genes 0.000 description 1
- 108060001064 Calcitonin Proteins 0.000 description 1
- 241000252095 Congridae Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 208000033830 Hot Flashes Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 1
- 208000010191 Osteitis Deformans Diseases 0.000 description 1
- 208000027868 Paget disease Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000013201 Stress fracture Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 238000011360 adjunctive therapy Methods 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229940062527 alendronate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000011444 antiresorptive therapy Methods 0.000 description 1
- 230000005744 arteriovenous malformation Effects 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 150000004663 bisphosphonates Chemical class 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229960004015 calcitonin Drugs 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 208000021863 corticosteroid-induced osteoporosis Diseases 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 201000003914 endometrial carcinoma Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 description 1
- 229940035638 gonadotropin-releasing hormone Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 208000027202 mammary Paget disease Diseases 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FRQMUZJSZHZSGN-HBNHAYAOSA-N medroxyprogesterone Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FRQMUZJSZHZSGN-HBNHAYAOSA-N 0.000 description 1
- 229960004616 medroxyprogesterone Drugs 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 210000001872 metatarsal bone Anatomy 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- DRVWQGBWPNZBTE-UHFFFAOYSA-N n-(2-methyl-4-nitrophenyl)-1-(2-methylpropyl)-3-thia-1-azaspiro[4.4]nonan-2-imine Chemical compound CC(C)CN1C(=NC=2C(=CC(=CC=2)[N+]([O-])=O)C)SCC11CCCC1 DRVWQGBWPNZBTE-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 208000001685 postmenopausal osteoporosis Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 201000010174 renal carcinoma Diseases 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 230000001457 vasomotor Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/42—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23190699A | 1999-01-14 | 1999-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200105253B true ZA200105253B (en) | 2002-09-05 |
Family
ID=22871101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200105253A ZA200105253B (en) | 1999-01-14 | 2001-06-26 | Substituted 2-arylimino heterocycles and compositions containing them for use as progesterone receptor binding agents. |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1144396A2 (cs) |
| JP (1) | JP2002534517A (cs) |
| KR (1) | KR20010089831A (cs) |
| CN (1) | CN1337955A (cs) |
| AR (1) | AR022214A1 (cs) |
| AU (1) | AU2708700A (cs) |
| BG (1) | BG105761A (cs) |
| BR (1) | BR9916999A (cs) |
| CA (1) | CA2359562A1 (cs) |
| CO (1) | CO5160338A1 (cs) |
| CZ (1) | CZ20012530A3 (cs) |
| GT (1) | GT200000003A (cs) |
| HU (1) | HUP0105134A2 (cs) |
| ID (1) | ID30514A (cs) |
| IL (1) | IL144031A0 (cs) |
| NO (1) | NO20013318L (cs) |
| SK (1) | SK10032001A3 (cs) |
| SV (1) | SV2002000005A (cs) |
| TR (1) | TR200102041T2 (cs) |
| WO (1) | WO2000042031A2 (cs) |
| ZA (1) | ZA200105253B (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8193252B1 (en) | 1999-08-31 | 2012-06-05 | Bayer Pharma AG | Mesoprogestins (progesterone receptor modulators) for the treatment and prevention of benign hormone dependent gynecological disorders |
| EA007854B1 (ru) * | 1999-08-31 | 2007-02-27 | Шеринг Акциенгезельшафт | Мезопрогестины (модуляторы рецептора прогестерона) в качестве средств лечения и предупреждения доброкачественных зависящих от гормонов гинекологических нарушений |
| HUP0202460A3 (en) * | 1999-08-31 | 2004-04-28 | Schering Ag | Mesoprogestins (progesterone receptor modulators) as a component of compositions for hormone replacement therapy (hrt) |
| ATE393150T1 (de) * | 1999-09-14 | 2008-05-15 | Shionogi & Co | 2-imino-1,3-thiazin-derivate |
| JPWO2001072723A1 (ja) * | 2000-03-28 | 2004-01-08 | 日本曹達株式会社 | オキサ（チア）ゾリジン誘導体および抗炎症薬 |
| EP1317456A2 (en) * | 2000-09-07 | 2003-06-11 | Bayer Corporation | Cyclic and acyclic amidines and pharmaceutical compositions containing them for use as progesterone receptor binding agents |
| CA2440186C (en) * | 2001-03-08 | 2009-01-13 | Shionogi & Co., Ltd. | Medicinal composition containing 1,3-thiazine derivative |
| US7189751B2 (en) | 2001-06-25 | 2007-03-13 | Nippon Soda Co., Ltd. | Oxa(thia)zolidine compounds, process for preparation thereof and anti-inflammatory agents |
| EP1465882B1 (en) | 2001-12-21 | 2011-08-24 | X-Ceptor Therapeutics, Inc. | Hetrocyclic modulators of nuclear receptors |
| US20060142387A1 (en) * | 2003-06-10 | 2006-06-29 | Rodolfo Cadilla | Chemical compounds |
| CN103382158B (zh) * | 2013-07-29 | 2015-11-18 | 张家港市大伟助剂有限公司 | 一种2-环戊基氨基乙醇的制备方法 |
| BR112022000188A2 (pt) * | 2019-07-10 | 2022-02-22 | Bayer Ag | Método para a preparação de 2-(fenilimino)-1,3-tiazolidin-4-onas |
| CN114507143A (zh) * | 2022-02-26 | 2022-05-17 | 江苏壹药新材料有限公司 | 一种2-乙基-1-氟-4-硝基苯的合成方法 |
| CN114671828B (zh) * | 2022-04-28 | 2024-05-31 | 蔚林新材料科技股份有限公司 | 一种3-甲基-2-噻唑硫酮的制备方法 |
| CN114957288B (zh) * | 2022-06-07 | 2024-02-13 | 苏州华道生物药业股份有限公司 | 一种盐酸四咪唑的合成方法 |
| CN115925559B (zh) * | 2022-11-11 | 2024-12-17 | 上海泰坦科技股份有限公司 | 一种1-氨基-1-环戊基甲醇的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670754A1 (de) * | 1966-09-27 | 1970-12-23 | Bayer Ag | Verfahren zur Herstellung von 2-Phenylimino-oxazolidinen |
| FR1510015A (fr) * | 1966-12-05 | 1968-01-19 | Aquitaine Petrole | Préparation d'imino-thiazolidines |
| DE1767335A1 (de) * | 1968-04-27 | 1971-09-02 | Bayer Ag | Anaesthetikum fuer Tiere |
| DE1963193A1 (de) * | 1969-12-17 | 1971-06-24 | Bayer Ag | N-substituierte 2-Arylimino-oxazolidine,Verfahren zu ihrer Herstellung und ihre Verwendung als Ektoparasiticide |
| FR2117337A5 (en) * | 1970-12-04 | 1972-07-21 | Eastman Kodak Co | Merocyanine dye sensitisers - contg basic and acidic gps for silver halide emulsions |
| US3787575A (en) * | 1970-12-17 | 1974-01-22 | Bayer Ag | N-substituted-2-arylimino-oxazolidines used as acaricides |
| GB1342232A (en) * | 1971-07-29 | 1974-01-03 | Bayer Ag | Aryliminothiazolidines a process for their preparation and their use as acaricides |
| CH614946A5 (cs) * | 1975-05-07 | 1979-12-28 | Ciba Geigy Ag | |
| DE2658138A1 (de) * | 1976-12-22 | 1978-07-06 | Bayer Ag | Substituierte 2-phenylimino-thiazolidine, verfahren zu ihrer herstellung sowie ihre verwendung als ektoparasitizide |
| DE2926771A1 (de) * | 1979-07-03 | 1981-01-15 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| DE3049460A1 (de) * | 1980-12-30 | 1982-07-29 | Hoechst Ag, 6000 Frankfurt | "thiazolinderivate, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
| DE3505432A1 (de) * | 1985-02-16 | 1986-08-21 | Hoechst Ag, 6230 Frankfurt | Pflanzenschutz- und schaedlingsbekaempfungsmittel auf der basis von thiazolidinderivaten sowie neue thiazolidinderivate und verfahren zu ihrer herstellung |
| EP0265162B1 (en) * | 1986-10-17 | 1991-03-06 | Stauffer Chemical Company | Iminooxazolidines, process of preparation and method of use |
| US4806653A (en) * | 1986-10-17 | 1989-02-21 | Stauffer Chemical Company | Process for preparation of iminooxazolidines |
| EP0270138B1 (en) * | 1986-11-04 | 1991-05-29 | Duphar International Research B.V | Substituted 2-phenylimino-oxazolidine compounds having herbicidal activity |
| WO1989004595A2 (en) * | 1987-11-19 | 1989-06-01 | The Upjohn Company | Ectoparasiticides |
-
1999
- 1999-12-14 HU HU0105134A patent/HUP0105134A2/hu unknown
- 1999-12-14 BR BR9916999-1A patent/BR9916999A/pt not_active IP Right Cessation
- 1999-12-14 TR TR2001/02041T patent/TR200102041T2/xx unknown
- 1999-12-14 JP JP2000593599A patent/JP2002534517A/ja active Pending
- 1999-12-14 AU AU27087/00A patent/AU2708700A/en not_active Abandoned
- 1999-12-14 CN CN99816464A patent/CN1337955A/zh active Pending
- 1999-12-14 IL IL14403199A patent/IL144031A0/xx unknown
- 1999-12-14 KR KR1020017008891A patent/KR20010089831A/ko not_active Withdrawn
- 1999-12-14 WO PCT/US1999/029601 patent/WO2000042031A2/en not_active Ceased
- 1999-12-14 ID IDW00200101749A patent/ID30514A/id unknown
- 1999-12-14 CA CA002359562A patent/CA2359562A1/en not_active Abandoned
- 1999-12-14 EP EP99968883A patent/EP1144396A2/en not_active Withdrawn
- 1999-12-14 SK SK1003-2001A patent/SK10032001A3/sk unknown
- 1999-12-14 CZ CZ20012530A patent/CZ20012530A3/cs unknown
-
2000
- 2000-01-06 AR ARP000100044A patent/AR022214A1/es unknown
- 2000-01-13 GT GT200000003A patent/GT200000003A/es unknown
- 2000-01-13 CO CO00001518A patent/CO5160338A1/es unknown
- 2000-01-13 SV SV2000000005A patent/SV2002000005A/es unknown
-
2001
- 2001-06-26 ZA ZA200105253A patent/ZA200105253B/en unknown
- 2001-07-04 NO NO20013318A patent/NO20013318L/no not_active Application Discontinuation
- 2001-08-01 BG BG105761A patent/BG105761A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000042031A2 (en) | 2000-07-20 |
| WO2000042031A3 (en) | 2000-11-09 |
| CA2359562A1 (en) | 2000-07-20 |
| SV2002000005A (es) | 2002-07-16 |
| TR200102041T2 (tr) | 2001-12-21 |
| EP1144396A2 (en) | 2001-10-17 |
| CN1337955A (zh) | 2002-02-27 |
| HUP0105134A2 (hu) | 2002-04-29 |
| CO5160338A1 (es) | 2002-05-30 |
| NO20013318D0 (no) | 2001-07-04 |
| IL144031A0 (en) | 2002-04-21 |
| KR20010089831A (ko) | 2001-10-08 |
| NO20013318L (no) | 2001-08-30 |
| AU2708700A (en) | 2000-08-01 |
| AR022214A1 (es) | 2002-09-04 |
| BR9916999A (pt) | 2001-10-30 |
| SK10032001A3 (sk) | 2002-05-09 |
| ID30514A (id) | 2001-12-13 |
| BG105761A (en) | 2002-03-29 |
| JP2002534517A (ja) | 2002-10-15 |
| CZ20012530A3 (cs) | 2002-02-13 |
| GT200000003A (es) | 2001-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200105253B (en) | Substituted 2-arylimino heterocycles and compositions containing them for use as progesterone receptor binding agents. | |
| US11833159B2 (en) | Non-hormonal steroid modulators of NF-kB for treatment of disease | |
| PL195772B1 (pl) | Zastosowanie prekursora sterydów płciowych w kombinacji z selektywnym modulatorem receptora estrogenu | |
| EP2582371B1 (en) | Methods of treating or preventing estrogen-related diseases | |
| AU2991301A (en) | Selective estrogen receptor modulators in combination with estrogens | |
| US10000525B2 (en) | Non-hormonal steroid modulators of NF-κB for treatment of disease | |
| WO2000043008A1 (en) | Anti-androgens and methods for treating disease | |
| WO2000041700A1 (en) | Use of estrogens and delta-gonadien-21-ol-3,20-diones in the treatment or prophylaxis of cerebral degenerative disorders | |
| US20030229072A1 (en) | Cyclic and acyclic amidines and pharmaceutical compositions containing them for use as progesterone receptor binning agents | |
| KR19980024568A (ko) | 프롤락틴 수준에 대한 중화 효과를 갖는 에스트로겐으로서의 8,9-데하이드로에스트론의 용도 | |
| AU2011253842A1 (en) | Medical Uses of a Selective Estrogen Receptor Modulator in Combination with Sex Steroid Precursors | |
| PL203438B1 (pl) | Kompozycja farmaceutyczna zawieraj aca dehydroepiandrosteron, pochodn a trifenyloetylenu i farmaceutycznie dopuszczaln a zaróbk e, zestaw i zastosowanie dehydroepiandrosteronu | |
| PL203439B1 (pl) | Kompozycja farmaceutyczna zawieraj aca dehydroepiandrosteron, pochodn a indolu i farmaceutycznie dopuszczaln a zaróbk e, zestaw i zastosowanie dehydroepiandrosteronu |