Claims
- 1. A compound of the formula: ##STR29## wherein R.sup.1 is H, C.sub.1 -C.sub.6 linear or branched alkyl, loweralkenyl, lower alkynyl, --X.sup.12 COOR.sup.6, --X.sup.11 -lower cycloalkyl, --X.sup.12 CN, or --X.sup.11 CX.sub.3.sup.10 ;
- R.sup.2 is H, loweralkyl, substituted or unsubstituted phenyl (wherein the substitutents may be 1 or 2 of halo, loweralkyl, loweralkoxy, loweralkylthio, carboxyl, carboxyloweralkyl, nitro, --CF.sub.3, or hydroxy), 2-, 3-, 4-pyridyl, ##STR30## --X.sup.12 SCH.sub.3, --x.sup.12 SOCH.sub.3, --X.sup.12 SO.sub.2 CH.sub.3, or --X.sup.12 COOR.sup.6 ;
- R.sup.3 is H,--X.sup.11 NR.sup.18 Xa.sup.11 R.sup.7, ##STR31## R.sup.6 is H, loweralkyl, lower cycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted phenylloweralkyl wherein the phenyl or phenylloweralkyl substituents may be 1 or 2 of halo, loweralkyl, loweralkoxy, nitro, or CF.sub.3 ;
- R.sup.7 is loweralkyl, lower cycloalkyl, X.sup.12 -cycloloweralkyl, wherein lower cycloalkyl encompasses C.sub.3 -C.sub.10 and may be mono or polycyclic, including bridged units, and such lower cycloalkyl units may be unsubstituted or independently substituted at one or two of the secondary carbons with the following substituents: ##STR32## R.sup.9 and R.sup.10 are independently H, --OH, or --CH.sub.3 ; R.sup.13 is H, loweralkyl, carboxyl, O, cycloloweralkyl, ##STR33## R.sup.14 is loweralkyl or phenylloweralkyl; R.sup.15 is H, loweralkyl, ##STR34## or --NH.sub.2 ; R.sup.18 is H, OH, OR.sup.13, or loweralkyl;
- p is O when its adjacent is unsaturated and 1 when its adjacent is saturated except that when R.sup.13 is O, p=1 and is unsaturated;
- r is 1 or 2;
- X.sup.1 is H, --NO.sub.2, CF.sub.3 CN, OH, loweralkyl, halo, loweralkylthio, loweralkoxy, --X.sup.11 COOR.sup.6, or --X.sup.11 NR.sup.4 R.sup.5 ;
- X.sup.2 and X.sup.3 are independently H, --OH, --NO.sub.2, halo, loweralkylthio, loweralkyl, or loweralkoxy;
- X.sup.7 is O, S, HH, or NR.sup.15 with the proviso that X.sup.7 can be NR.sup.15 only when R.sup.1 is not H;
- X.sup.9 and X.sub.a.sup.9 are independently NR.sup.18 or O;
- X.sup.10 is F, Cl, or Br;
- X.sup.11 and X.sub.a.sup.11 are independently absent or C.sub.1-4 linear or branched alkylidene; X.sup.12 os C.sub.1-4 linear or branched alkyl;
- is a saturated or unsaturated bond;
- and the pharmaceutically acceptable salts thereof, with the proviso that R.sup.3 is H when and only when R.sup.13 is ##STR35##
- 2. A compound of claim 1 wherein: wherein:
- R.sup.1 is H, C.sub.1 -C.sub.6 linear or branched alkyl;
- R.sup.2 is substituted or unsubstituted phenyl (wherein the substitutents may be 1 or 2 of halo, loweralkyl, loweralkoxy, loweralkylthio, carboxyl, carboxyloweralkyl, nitro, --CF.sub.3, or hydroxy);
- R.sup.3 is --X.sup.11 NR.sup.18 Xa.sup.11 R.sup.7, ##STR36## R.sup.6 is H, loweralkyl, lower cycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted phenylloweralkyl wherein the phenyl or phenylloweralkyl substituents may be 1 or 2 of halo, loweralkyl, loweralkoxy, nitro, or CF.sub.3 ;
- R.sup.7 is loweralkyl, lower cycloalkyl, X.sup.12 -lower cycloalkyl, wherein lower cycloalkyl encompasses C.sub.3 -C.sub.10 and may be mono or polycyclic, including bridged units, and such cycloloweralkyl units may be unsubstituted or independently substituted at one or two of the secondary carbons with the following substituents: ##STR37## R.sup.9 and R.sup.10 are independently H; R.sup.13 is H;
- R.sup.14 is loweralkyl or phenylloweralkyl;
- R.sup.15 is H, loweralkyl, ##STR38## or --NH.sub.2 ; R.sup.18 is H, OH, or loweralkyl;
- p is 0 when its adjacent is unsaturated and 1 when its adjacent is saturated;
- r is 1;
- X.sup.1 is H;
- X.sup.7 is O;
- X.sup.9 and X.sub.a.sup.9 are independently NR.sup.18 or O;
- X.sup.11 and X.sub.a.sup.11 are independently absent or C.sub.1-4 linear or branched alkyl;
- X.sup.12 is C.sub.1-4 linear or branched alkyl
- is a saturated or unsaturated bond;
- and the pharmaceutically acceptable salts thereof.
- 3. A compound selected from the group consisting of:
- (+/-)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-N'-TRICYCLO(3.3.1.1(3,7))DEC-2-YL-UREA
- (+)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-N'-TRICYCLO(3.3.1.1(3,7))DEC-2-YL-UREA
- (R)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-N'-TRICYCLO(3.3.1.1(3,7))DEC-1-YL-UREA
- (+/-)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-TRICYCLO(3.3.1.1(3,7))DECANE-1-CARBOXAMIDE
- (+/-)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-TRICYCLO(3.3.1.1(3,7))DECANE-1-ACETAMIDE)
- (+/-)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-N'-TRICYCLO(3.3.1.1(3,7))DEC-1-YL-METHYL)-UREA
- (+/-)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-3-METHYLTRICYCLO(3.3.1.1(3.7))DECANE-1-ACETAMIDE
- (1S)-(1.ALPHA.(RS),4.ALPHA.))-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-7,7-DIMETHYL-2-OXO-BICYCLO(2.2.1)HEPTANE-1-METHANESULFONAMIDE
- (1R-(1.ALPHA.(RS),4.ALPHA.))-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H1,4-BENZODIAZEPIN-3-YL)-7,7-DIMETHYL-2-OXO-BICYCLO(2.2.1)HEPTANE-1-METHANESULFONAMIDE
- (+/-)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-N'-TRICYCLO(3.3.1.0(3,7))DEC-2-YL-UREA
- ALPHA.-((((2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)AMINO)CARBONYL)AMINO)BENZENEACETIC ACID ETHYL ESTER, ALPHA ISOMER
- (+/-)-1,2,3,5-TETRAHYDRO-1-METHYL-2-OXO-5-PHENYL-N-(TRICYCLO(3.3.1.1.(3,7))DEC-1-YLMETHYL)-4H-1,4-BENZODIAZEPINE-4-CARBOXAMIDE
- (+/-)-1,2,3,5-TETRAHYDRO-1-METHYL-2-OXO-5-PHENYL-N-TRICYCLO(3.3.1.1(3,7))DEC-2-YL-4H-1,4-BENZODIAZEPINE-4-CARBOXAMIDE
- (1R-(1.ALPHA.(R*),4.ALPHA.))-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-7,7-DIMETHYL-2-OXO-BICYCLO(2.2.1)HEPTANE-1-METHANESULFONAMIDE
- (1R-(1.ALPHA.(S*),4.ALPHA.))-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-7,7-DIMETHYL-2-OXO-BICYCLO(2.2.1)HEPTANE-1-METHANESULFONAMIDE
- N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-2-HYDROXY-7,7-DIMETHYL-BICYCLO(2.2.1)HEPTANE-1-METHANESULFONAMIDE, ISOMER A AND ISOMER B
- N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-2-HYDROXY-7,7-DIMETHYL-BICYCLO(2.2.1)HEPTANE-1-METHANESULFONAMIDE,
- [3(S)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)]-2-OXO-1,7,7-TRIMETHYL-BICYCLO(2.2.1)HEPTANE-3-ACETAMIDE
- [3(R)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)]-2-OXO-1,7,7-TRIMETHYL-BICYCLO(2.2.1)HEPTANE-3-ACETAMIDE
- (1S-(1.ALPHA.(S*),4.ALPHA.))-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-7,7-DIMETHYL-2-OXO-BICYCLO(2.2.1)HEPTANE-1-METHANESULFONAMIDE
- (1S-(1.ALPHA.(R*),4.ALPHA.))-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-7,7-DIMETHYL-2-OXO-BICYCLO(2.2.1)HEPTANE-1-METHANESULFONAMIDE
- [3(S)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)]-2-HYDROXY-1,7,7-TRIMETHYL-BICYCLO(2.2.1)HEPTANE-3-ACETAMIDE, ISOMER A AND ISOMER B
- [3(R)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)]-2-OXO-1,7,7-TRIMETHYLBICYCLO(2.2.1)HEPTANE-3-CARBOXAMIDE
- 4. A compound of claim 3 which is:
- (+)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-N'-TRICYCLO(3.3.1.1(3,7))DEC-2-YL-UREA
- (R)-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-N'-TRICYCLO(3.3.1.1(3,7))DEC-1-YL-UREA
- (1R-(1.ALPHA.(S*),4.ALPHA.))-N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-7,7-DIMETHYL-2-OXO-BICYCLO(2.2.1)HEPTANE-1-METHANESULFONAMIDE
- N-(2,3-DIHYDRO-1-METHYL-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPIN-3-YL)-2-HYDROXY-7,7-DIMETHYL-BICYCLO(2.2.1)HEPTANE-1-METHANESULFONAMIDE.
- 5. A pharmaceutical composition which comprises a pharmaceutically-acceptable carrier and an amount of the compound as claimed in claim 1 effective to prevent pre-term labor in a mammal in need thereof.
- 6. A pharmaceutical composition which comprises a pharmaceutically-acceptable carrier and an amount of the compound as claimed in claim 1 effective to treat dysmenorrhea in a mammal in need thereof.
- 7. A pharmaceutical composition which comprises a pharmaceutically acceptable carrier and an amount of the compound as claimed in claim 1 effective to stop labor preparatory to caesarean delivery.
Parent Case Info
This is a continuation of application Ser. No. 07/417,412, filed on Oct. 5, 1989, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4628084 |
Book et al. |
Dec 1986 |
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4820834 |
Evans et al. |
Apr 1989 |
|
Non-Patent Literature Citations (1)
Entry |
Journal of Medicinal Chemistry, 32, 1 (1989), Bock, et al. |
Continuations (1)
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Number |
Date |
Country |
Parent |
417412 |
Oct 1989 |
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